From c12012a83a5b02a315e42be23dec3e471c8d87af Mon Sep 17 00:00:00 2001
From: tlongwell-block <109685178+tlongwell-block@users.noreply.github.com>
Date: Thu, 16 Jul 2026 20:28:16 -0400
Subject: [PATCH] Add link and video right-click Download/Copy menus (bug-bash
 media lane)
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

Buzz renders inside a native webview whose default context menu has no
useful link or media actions, so right-clicking a link was a no-op
(#02ef9f1b) and videos had no Download at all. This adds custom in-app
context menus for links and inline videos, and dedupes the existing
image menu into a single shared primitive.

- New `MediaContextMenu` primitive (portal menu + deferred-dismiss hook),
  reused three ways: image (Copy/Download), link (Open/Copy), video
  (Download/Copy). Each variant emits a distinct data attribute
  (`data-image-context-menu` / `data-link-context-menu` /
  `data-video-context-menu`) plus the shared `data-media-context-menu`
  marker, so e2e locators target one surface without aliasing another;
  the image variant additionally carries `data-image-lightbox-controls`
  for the in-lightbox dismiss guard.
- Links: `ExternalLinkAnchor` adds Open link (OS opener) / Copy link.
- Videos: the `useVideoContextMenu` hook owns the inline right-click menu's
  state and actions — Download video (reuses the existing `download_file`
  command) and Copy link — keeping that logic out of the large `VideoPlayer`
  and out of the pure `videoDownload.ts` helpers.

Render classification and download eligibility are independent (pure,
DOM-free helpers in `markdown/mediaEntry.ts`):

- `isVideoMedia` classifies from the imeta MIME (`video/*`), authoritative
  when present, with a legacy path-extension fallback for pre-MIME events.
  Previously only `.mp4` was recognized, so relay `.webm`/`.mov` fell into
  the image renderer and Tyler's video Download was absent. The relay-media
  proxy regex is widened to `mp4|webm|mov` to match.
- `isRelayDownloadable` gates Download on relay `/media/` origin, not mere
  URL presence, so an external video renders and offers Copy link but omits
  Download (which the Rust SSRF gate would reject anyway). The original
  relay `src` is the download URL, never the rewritten proxy `resolvedSrc`.

Download eligibility is reactive and fails closed. The relay origin resolves
asynchronously and is commonly still null on first render; a synchronous read
would freeze eligibility, so `mediaUrl.ts` exposes the origin as an observable
(`subscribeRelayOrigin` + `getCachedRelayOrigin`) consumed via
`useRelayOrigin()` (`useSyncExternalStore`). `MarkdownVideoPlayer` reads it, so
eligibility recomputes when the origin resolves and on workspace switch.
`isRelayDownloadable` now returns false for an unresolved origin (fail closed)
rather than optimistically true — before, an off-relay `/media/` URL wrongly
showed Download until resolution. A generation token (`beginRelayOriginFetch`)
ensures an in-flight origin fetch from a previous community can never publish
after a workspace switch. The origin fetch is retried inside the port poll loop
(a single fire-and-forget attempt could fail before the Tauri bridge was ready
and leave the origin null forever), and each poll invoke is bounded by the
remaining deadline (`withDeadline`) so a never-settling IPC call cannot hang
startup past the 5s budget.

Redirect-hop SSRF: authenticated media *download* fetches use a dedicated
no-redirect client built by `build_media_fetch_client() -> Result`
(`redirect::Policy::none()`). `build_app_state()` calls `.expect(...)` so a
build failure panics loudly at startup rather than silently degrading to a
redirect-following client (fail closed, not fail open). A relay 3xx is returned
verbatim and mapped by `redirect_refusal_error` to an actionable "redirect
refused" error — not a generic relay failure and never a followed cross-origin
fetch of the minted media Authorization header. The app-wide `http_client` is
unchanged.

Follow-up (NOT fixed here — this PR hardens the download path only, and
must not be read as making rendering redirect-safe): the media *rendering*
path shares the same exposure. The axum proxy in
`src-tauri/src/media_proxy.rs` and the `buzz-media://` protocol handler
(registered in `src-tauri/src/lib.rs`) both mint a media Authorization
header and follow redirects, so a relay 3xx to a private/off-origin target
would forward that header cross-origin. It is left untouched here because
it is the passive streaming path (a legitimate relay CDN-offload redirect
would break `<video>`/`<img>`), it is broader than this Download lane, and
scope was deliberately kept narrow.

Tests: `mediaEntry.test.mjs` (MIME/extension classification incl. uppercase,
query strings, MIME-with-extensionless URL; relay/off-relay/malformed download
eligibility; fail-closed unresolved origin + both resolution transitions);
`mediaUrl.test.mjs` (observable store: publish/notify, notify-only-on-change,
per-listener unsubscribe, the A->reset->B late-A race, transient-failure retry
publishes exactly once, reset-mid-retry discards the stale generation, and
`withDeadline` incl. a never-settling invoke, an early rejection, and a
late rejection after timeout staying observed); `videoDownload.test.mjs`
(save-dialog filename fallback); Rust `validate_download_url` mp4/webm parity
and private-host rejection, a loopback no-redirect test proving a 302 is not
followed, exactly one request is issued, and the command-facing error
identifies the refused redirect, plus `build_media_fetch_client` constructs
with the no-redirect policy and `redirect_refusal_error` only fires for 3xx;
e2e distinct-selector probes for link (Open/Copy via a genuine bubbling
contextmenu event), relay video (Download appears once the origin resolves),
and off-relay video (Copy only, never Download), each asserting no cross-variant
attributes. 3031 desktop unit tests, whole-package
`cargo test -p buzz-desktop` (1445 lib + 3 integration), typecheck, lint, and
`pnpm build` all clean. Note: a real authenticated saved-byte download check
remains for the integrated Desktop tip (can't drive a live relay from this lane).

Co-authored-by: Dawn (sprout agent) <c6237ef84fa537c78dcee78efd2d4e59f728859c7f194da42ac51ededfa0be05@sprout-oss.stage.blox.sqprod.co>
Signed-off-by: tlongwell-block <109685178+tlongwell-block@users.noreply.github.com>
---
 desktop/scripts/check-file-sizes.mjs          |  16 +-
 desktop/src-tauri/src/app_state.rs            |  35 +++
 .../src-tauri/src/commands/media_download.rs  | 168 ++++++++++++-
 desktop/src/shared/lib/mediaUrl.test.mjs      | 182 +++++++++++++-
 desktop/src/shared/lib/mediaUrl.ts            | 172 ++++++++++++--
 desktop/src/shared/lib/useRelayOrigin.ts      |  24 ++
 desktop/src/shared/ui/VideoPlayer.tsx         |  17 +-
 desktop/src/shared/ui/markdown.tsx            | 223 +++++++++---------
 .../ui/markdown/MarkdownVideoPlayer.tsx       |  15 ++
 .../shared/ui/markdown/MediaContextMenu.tsx   | 111 +++++++++
 .../shared/ui/markdown/mediaEntry.test.mjs    | 111 +++++++++
 desktop/src/shared/ui/markdown/mediaEntry.ts  |  77 ++++++
 desktop/src/shared/ui/useVideoContextMenu.tsx |  83 +++++++
 desktop/src/shared/ui/videoDownload.test.mjs  |  24 ++
 desktop/src/shared/ui/videoDownload.ts        |  20 ++
 .../e2e/image-attachment-gallery.spec.ts      |   8 +
 desktop/tests/e2e/video-attachment.spec.ts    | 145 ++++++++++++
 17 files changed, 1299 insertions(+), 132 deletions(-)
 create mode 100644 desktop/src/shared/lib/useRelayOrigin.ts
 create mode 100644 desktop/src/shared/ui/markdown/MediaContextMenu.tsx
 create mode 100644 desktop/src/shared/ui/markdown/mediaEntry.test.mjs
 create mode 100644 desktop/src/shared/ui/markdown/mediaEntry.ts
 create mode 100644 desktop/src/shared/ui/useVideoContextMenu.tsx
 create mode 100644 desktop/src/shared/ui/videoDownload.test.mjs
 create mode 100644 desktop/src/shared/ui/videoDownload.ts

diff --git a/desktop/scripts/check-file-sizes.mjs b/desktop/scripts/check-file-sizes.mjs
index b787e7f9a..e14a6efe9 100644
--- a/desktop/scripts/check-file-sizes.mjs
+++ b/desktop/scripts/check-file-sizes.mjs
@@ -368,7 +368,15 @@ const overrides = new Map([
   ["src/features/settings/ui/ProfileSettingsCard.tsx", 1033],
   // keyring-dev-isolation: keyring_service() fn (7 lines) replaces the const
   // to return "buzz-desktop-dev" in debug builds. Load-bearing isolation fix.
-  ["src-tauri/src/app_state.rs", 1042],
+  // +10 (1042 -> 1052): media_fetch_client with redirect::Policy::none() so a
+  // relay 3xx cannot forward the minted auth header cross-origin (SSRF fix).
+  // +16 (1052 -> 1068): extracted that client into `build_media_fetch_client()`
+  // -> Result so the fail-closed invariant is testable (no silent redirect-
+  // following fallback; startup panics loudly instead). The function belongs
+  // here beside `build_app_state` and its sibling client; its doc comment
+  // carries the load-bearing SSRF rationale. Extraction would only relocate,
+  // not reduce, the security-critical code.
+  ["src-tauri/src/app_state.rs", 1068],
   // multi-slot splitting + no-op suppression (#1309): the ReadStateManager
   // class grew from ~700 lines to ~1019 with the addition of
   // splitContextsIntoBudgetedSlots (pure fn + 5 tests), publishSplitSlots,
@@ -396,7 +404,11 @@ const overrides = new Map([
   // large shared renderers cannot grow further while follow-up splits land.
   // +33 for config-nudge detect-and-render + author-auth gate (normalizePubkey guard).
   ["src/shared/ui/markdown.tsx", 2152],
-  ["src/shared/ui/VideoPlayer.tsx", 2199],
+  // +15 (2199 -> 2214): the video right-click Download/Copy menu's props,
+  // hook wiring, and render slot. The stateful menu logic (~52 lines) was
+  // extracted to useVideoContextMenu.tsx; what remains here is the component's
+  // public interface (downloadUrl/filename props) and cannot move out.
+  ["src/shared/ui/VideoPlayer.tsx", 2214],
   ["src/shared/ui/sidebar.tsx", 1042],
   // permission-outcome (fix #1381 regression): pendingPermissions state map,
   // describePermissionOutcome helper, jsonRpcId key helper (handles both
diff --git a/desktop/src-tauri/src/app_state.rs b/desktop/src-tauri/src/app_state.rs
index 0246c0a61..6d509318e 100644
--- a/desktop/src-tauri/src/app_state.rs
+++ b/desktop/src-tauri/src/app_state.rs
@@ -18,6 +18,15 @@ use crate::managed_agents::ManagedAgentProcess;
 pub struct AppState {
     pub keys: Mutex<Keys>,
     pub http_client: reqwest::Client,
+    /// A no-redirect client for authenticated relay media fetches (download,
+    /// clipboard copy, snapshot, editor). Every caller pre-validates the URL
+    /// origin, but the app-wide `http_client` follows redirects by default, so
+    /// a relay `/media/` URL returning a 3xx to an off-origin or private host
+    /// would forward the minted media Authorization header across origins —
+    /// a redirect-hop SSRF. This client treats any 3xx as a non-success
+    /// response (surfaced as an error) so the auth token never leaves the
+    /// validated relay origin.
+    pub media_fetch_client: reqwest::Client,
     /// Workspace-provided relay URL override. Set by `apply_workspace` on app
     /// init and takes priority over env vars and compile-time defaults.
     pub relay_url_override: Mutex<Option<String>>,
@@ -137,6 +146,27 @@ fn identity_from_env() -> Option<Keys> {
     }
 }
 
+/// Build the no-redirect HTTP client used for authenticated relay media
+/// fetches (download / copy).
+///
+/// This client is a security boundary, not a convenience: it carries a minted
+/// media `Authorization` header, so it MUST NOT follow redirects. A relay 3xx
+/// to an off-origin or private host would otherwise forward that header across
+/// origins (a redirect-hop SSRF). `redirect::Policy::none()` returns the 3xx
+/// verbatim so the caller can reject it.
+///
+/// Returned as a `Result` so the fail-closed invariant is testable — callers
+/// must never substitute a redirect-following client on build failure. Shares
+/// the localhost `resolve`/pool config with the app-wide `http_client`.
+pub fn build_media_fetch_client() -> reqwest::Result<reqwest::Client> {
+    reqwest::Client::builder()
+        .resolve("localhost", std::net::SocketAddr::from(([127, 0, 0, 1], 0)))
+        .pool_idle_timeout(std::time::Duration::from_secs(10))
+        .pool_max_idle_per_host(1)
+        .redirect(reqwest::redirect::Policy::none())
+        .build()
+}
+
 pub fn build_app_state() -> AppState {
     // Env var takes precedence (dev/CI). If absent, resolve_persisted_identity()
     // in setup() will replace the ephemeral placeholder with a persisted key.
@@ -159,6 +189,11 @@ pub fn build_app_state() -> AppState {
             .pool_max_idle_per_host(1)
             .build()
             .unwrap_or_else(|_| reqwest::Client::new()),
+        media_fetch_client: build_media_fetch_client().expect(
+            "media_fetch_client must build with redirect::Policy::none(); a \
+             redirect-following fallback would forward the minted media auth \
+             header across origins (redirect-hop SSRF)",
+        ),
         relay_url_override: Mutex::new(None),
         managed_agent_restore_pending: AtomicBool::new(false),
         shutdown_started: AtomicBool::new(false),
diff --git a/desktop/src-tauri/src/commands/media_download.rs b/desktop/src-tauri/src/commands/media_download.rs
index dcc57819b..1ba691597 100644
--- a/desktop/src-tauri/src/commands/media_download.rs
+++ b/desktop/src-tauri/src/commands/media_download.rs
@@ -264,14 +264,35 @@ async fn fetch_blob_bytes(url: &str, state: &State<'_, AppState>) -> Result<Vec<
     fetch_blob_bytes_with_cap(url, state, MAX_DOWNLOAD_BYTES).await
 }
 
+/// The command-facing error for a media-fetch response status, or `None` if
+/// the status is success and the body should be read.
+///
+/// A no-redirect client surfaces a relay 3xx as a redirection status rather
+/// than following it; that is reported explicitly as a redirect (not a bare
+/// "relay returned 302") so the failure is actionable and cannot be mistaken
+/// for an ordinary relay error — following it would forward the minted media
+/// auth header across origins. Pulled out of `fetch_blob_bytes_with_cap` so
+/// the redirect-refusal message is unit-testable without a Tauri `State`.
+fn redirect_refusal_error(status: reqwest::StatusCode) -> Option<String> {
+    status.is_redirection().then(|| {
+        format!(
+            "media fetch refused: relay returned a {status} redirect, which is \
+             not followed for authenticated downloads (redirect-hop SSRF guard)"
+        )
+    })
+}
+
 /// Core streaming fetcher with a caller-supplied byte cap.
 async fn fetch_blob_bytes_with_cap(
     url: &str,
     state: &State<'_, AppState>,
     cap: u64,
 ) -> Result<Vec<u8>, String> {
-    // Fetch bytes via the app's HTTP client (goes through WARP tunnel).
-    let mut req = state.http_client.get(url).timeout(DOWNLOAD_TIMEOUT);
+    // Fetch bytes via the no-redirect media client (goes through WARP tunnel).
+    // A no-redirect client keeps the minted media auth token from being
+    // forwarded across origins by a relay-issued 3xx (redirect-hop SSRF); a
+    // 3xx is returned verbatim and rejected by the `is_success` check below.
+    let mut req = state.media_fetch_client.get(url).timeout(DOWNLOAD_TIMEOUT);
 
     // Every caller pre-validates `url` against the relay origin via
     // `validate_download_url`, satisfying the mint_media_get_auth safety
@@ -283,6 +304,10 @@ async fn fetch_blob_bytes_with_cap(
 
     let resp = req.send().await.map_err(|e| classify_request_error(&e))?;
 
+    if let Some(err) = redirect_refusal_error(resp.status()) {
+        return Err(err);
+    }
+
     if !resp.status().is_success() {
         return Err(relay_error_message(resp).await);
     }
@@ -826,4 +851,143 @@ mod tests {
         assert!(result.is_err());
         assert!(result.unwrap_err().contains("/media/"));
     }
+
+    // Video Download reuses `download_file`, which runs the same
+    // `validate_download_url` gate as image download. `validate_download_url`
+    // is extension-agnostic (it only checks scheme, origin, and the `/media/`
+    // path prefix), so a relay-hosted mp4/webm passes exactly like an image,
+    // and an off-relay or private-host video is rejected exactly like an
+    // off-relay image. These cases pin that parity so a future change can't
+    // silently narrow the video download path's SSRF protection.
+    #[test]
+    fn test_validate_download_url_valid_relay_video_mp4() {
+        assert!(validate_download_url(
+            "https://relay.example.com/media/abcdef1234567890.mp4",
+            RELAY_BASE,
+        )
+        .is_ok());
+    }
+
+    #[test]
+    fn test_validate_download_url_valid_relay_video_webm() {
+        assert!(
+            validate_download_url("https://relay.example.com/media/abc123.webm", RELAY_BASE)
+                .is_ok()
+        );
+    }
+
+    #[test]
+    fn test_validate_download_url_non_relay_video_rejected() {
+        let result = validate_download_url("https://evil.example.com/media/clip.mp4", RELAY_BASE);
+        assert!(result.is_err());
+        assert!(result.unwrap_err().contains("relay origin"));
+    }
+
+    #[test]
+    fn test_validate_download_url_private_host_video_rejected() {
+        // Off-relay private host serving a video must be rejected before any
+        // fetch — same SSRF gate as image download.
+        let result = validate_download_url("http://127.0.0.1/media/clip.mp4", RELAY_BASE);
+        assert!(result.is_err());
+        assert!(result.unwrap_err().contains("relay origin"));
+    }
+
+    /// Redirect-hop SSRF guard: the media fetch client must NOT follow a 3xx,
+    /// and the command-facing error must identify the refused redirect.
+    ///
+    /// `validate_download_url` only vets the *initial* URL, so a relay that
+    /// returned a redirect to an off-origin or private host would, under a
+    /// redirect-following client, forward the minted media Authorization
+    /// header across origins. The client `build_media_fetch_client()` produces
+    /// (the same one `fetch_blob_bytes_with_cap` uses via `AppState`) is built
+    /// with `redirect::Policy::none()`, so the 302 comes back verbatim and
+    /// `redirect_refusal_error` — the same mapping the command applies — turns
+    /// it into an actionable redirect error, not a silent cross-origin fetch.
+    ///
+    /// A loopback `std::net::TcpListener` (no extra tokio feature) serves one
+    /// raw `302` pointing at an off-origin target and records how many
+    /// connections it accepts.
+    #[tokio::test]
+    async fn media_fetch_client_does_not_follow_redirects() {
+        use std::io::{Read, Write};
+        use std::sync::atomic::{AtomicUsize, Ordering};
+        use std::sync::Arc;
+
+        let listener = std::net::TcpListener::bind("127.0.0.1:0").unwrap();
+        let addr = listener.local_addr().unwrap();
+        let connections = Arc::new(AtomicUsize::new(0));
+
+        let server_connections = Arc::clone(&connections);
+        let server = std::thread::spawn(move || {
+            // Accept exactly one connection; if the client followed the
+            // redirect it would open a second one to the (unrelated) target,
+            // but that target is never this server, so a second accept here
+            // would only happen on an unexpected retry. We serve one 302 and
+            // return, so the count stays at 1 for a compliant no-redirect client.
+            if let Ok((mut stream, _)) = listener.accept() {
+                server_connections.fetch_add(1, Ordering::SeqCst);
+                let mut buf = [0u8; 1024];
+                let _ = stream.read(&mut buf);
+                let response = "HTTP/1.1 302 Found\r\n\
+                     Location: http://169.254.169.254/latest/meta-data/\r\n\
+                     Content-Length: 0\r\n\
+                     Connection: close\r\n\r\n";
+                let _ = stream.write_all(response.as_bytes());
+                let _ = stream.flush();
+            }
+        });
+
+        // Drive the exact client the command path uses, not an ad-hoc one.
+        let client = crate::app_state::build_media_fetch_client()
+            .expect("media fetch client must build with no-redirect policy");
+        let resp = client
+            .get(format!("http://{addr}/media/clip.mp4"))
+            .timeout(std::time::Duration::from_secs(5))
+            .send()
+            .await
+            .expect("request should complete without following the redirect");
+
+        // The 302 is returned verbatim — not the 169.254.x target's response.
+        assert_eq!(resp.status().as_u16(), 302);
+        assert!(!resp.status().is_success());
+
+        // The command maps that status through `redirect_refusal_error`; the
+        // user-facing error must name the redirect, not read as a generic
+        // relay failure.
+        let err = redirect_refusal_error(resp.status())
+            .expect("a 3xx must map to a redirect-refusal error");
+        assert!(
+            err.contains("redirect") && err.contains("302"),
+            "error must identify the refused 302 redirect, got: {err}",
+        );
+
+        server.join().unwrap();
+        assert_eq!(
+            connections.load(Ordering::SeqCst),
+            1,
+            "exactly one request must be issued — the redirect must not be followed",
+        );
+    }
+
+    #[test]
+    fn build_media_fetch_client_succeeds_with_no_redirect_policy() {
+        // The fail-closed invariant: construction must not silently degrade to
+        // a redirect-following client. If this ever starts failing, startup
+        // panics loudly (see `build_app_state`) rather than substituting an
+        // insecure client.
+        assert!(
+            crate::app_state::build_media_fetch_client().is_ok(),
+            "media fetch client must build; a redirect-following fallback is forbidden",
+        );
+    }
+
+    #[test]
+    fn redirect_refusal_error_only_fires_for_3xx() {
+        // 3xx → redirect-identifying error; success/non-3xx → None (fall
+        // through to the normal success or relay-error handling).
+        assert!(redirect_refusal_error(reqwest::StatusCode::FOUND).is_some());
+        assert!(redirect_refusal_error(reqwest::StatusCode::TEMPORARY_REDIRECT).is_some());
+        assert!(redirect_refusal_error(reqwest::StatusCode::OK).is_none());
+        assert!(redirect_refusal_error(reqwest::StatusCode::NOT_FOUND).is_none());
+    }
 }
diff --git a/desktop/src/shared/lib/mediaUrl.test.mjs b/desktop/src/shared/lib/mediaUrl.test.mjs
index e436f9685..36a357eba 100644
--- a/desktop/src/shared/lib/mediaUrl.test.mjs
+++ b/desktop/src/shared/lib/mediaUrl.test.mjs
@@ -1,7 +1,14 @@
 import assert from "node:assert/strict";
 import { test } from "node:test";
 
-import { mediaProxyUrl } from "./mediaUrl.ts";
+import {
+  beginRelayOriginFetch,
+  getCachedRelayOrigin,
+  mediaProxyUrl,
+  resetMediaCaches,
+  subscribeRelayOrigin,
+  withDeadline,
+} from "./mediaUrl.ts";
 
 const HASH = "a".repeat(64);
 
@@ -11,3 +18,176 @@ test("mediaProxyUrl: uses the IPv4 loopback literal for the localhost proxy", ()
     `http://127.0.0.1:54321/media/${HASH}.png`,
   );
 });
+
+test("relay-origin store: a resolved origin publishes and notifies subscribers", () => {
+  resetMediaCaches();
+  let notifications = 0;
+  const unsubscribe = subscribeRelayOrigin(() => notifications++);
+
+  const publish = beginRelayOriginFetch();
+  publish("https://relay.example");
+
+  assert.equal(getCachedRelayOrigin(), "https://relay.example");
+  assert.equal(notifications, 1);
+
+  unsubscribe();
+  resetMediaCaches();
+});
+
+test("relay-origin store: unsubscribe removes exactly its own listener", () => {
+  resetMediaCaches();
+  let kept = 0;
+  let dropped = 0;
+  const unsubscribeKept = subscribeRelayOrigin(() => kept++);
+  const unsubscribeDropped = subscribeRelayOrigin(() => dropped++);
+
+  // Dropping one listener must not affect the other.
+  unsubscribeDropped();
+  beginRelayOriginFetch()("https://relay.example");
+  assert.equal(kept, 1);
+  assert.equal(dropped, 0);
+
+  unsubscribeKept();
+  resetMediaCaches();
+});
+
+test("relay-origin store: reset notifies only on an actual snapshot change", () => {
+  resetMediaCaches();
+  let notifications = 0;
+  const unsubscribe = subscribeRelayOrigin(() => notifications++);
+
+  // Origin already null → reset is a no-op for listeners.
+  resetMediaCaches();
+  assert.equal(notifications, 0);
+
+  // Now resolve, then reset: the reset clears a non-null origin, so it fires.
+  beginRelayOriginFetch()("https://relay.example");
+  assert.equal(notifications, 1);
+  resetMediaCaches();
+  assert.equal(getCachedRelayOrigin(), null);
+  assert.equal(notifications, 2);
+
+  unsubscribe();
+});
+
+test("relay-origin store: a late fetch from the previous community never regresses the snapshot", () => {
+  resetMediaCaches();
+  const unsubscribe = subscribeRelayOrigin(() => {});
+
+  // Community A starts a fetch, then the user switches workspaces (reset),
+  // then community B starts its own fetch.
+  const publishA = beginRelayOriginFetch();
+  resetMediaCaches();
+  const publishB = beginRelayOriginFetch();
+
+  // A resolves late — its generation is stale, so it must be discarded.
+  publishA("https://relay-a.example");
+  assert.equal(getCachedRelayOrigin(), null);
+
+  // B resolves — it is current, so it wins.
+  publishB("https://relay-b.example");
+  assert.equal(getCachedRelayOrigin(), "https://relay-b.example");
+
+  // A late duplicate from A after B must still not clobber B.
+  publishA("https://relay-a.example");
+  assert.equal(getCachedRelayOrigin(), "https://relay-b.example");
+
+  unsubscribe();
+  resetMediaCaches();
+});
+
+test("relay-origin store: a failed attempt then a later success publishes exactly once", () => {
+  // Mirrors the `fetchProxyPort` retry loop: each poll attempt calls
+  // `beginRelayOriginFetch()` and only publishes if the invoke resolves. An
+  // early attempt whose invoke rejects (Tauri bridge not ready) never calls its
+  // publisher, so nothing is published; a later attempt succeeds and publishes.
+  resetMediaCaches();
+  let notifications = 0;
+  const unsubscribe = subscribeRelayOrigin(() => notifications++);
+
+  // Attempt 1: invoke rejects — publisher is never invoked.
+  beginRelayOriginFetch();
+  assert.equal(getCachedRelayOrigin(), null);
+  assert.equal(notifications, 0);
+
+  // Attempt 2: invoke resolves — publishes once, notifies once.
+  beginRelayOriginFetch()("https://relay.example");
+  assert.equal(getCachedRelayOrigin(), "https://relay.example");
+  assert.equal(notifications, 1);
+
+  unsubscribe();
+  resetMediaCaches();
+});
+
+test("relay-origin store: a reset between a failed attempt and its late success discards the stale result", () => {
+  // A workspace switch (reset) during the retry sequence must invalidate a
+  // still-in-flight attempt from the previous community, even if that attempt
+  // eventually resolves after the switch.
+  resetMediaCaches();
+  const unsubscribe = subscribeRelayOrigin(() => {});
+
+  // Attempt from community A begins, then the user switches (reset), then a
+  // fresh attempt from community B begins and succeeds.
+  const publishA = beginRelayOriginFetch();
+  resetMediaCaches();
+  beginRelayOriginFetch()("https://relay-b.example");
+  assert.equal(getCachedRelayOrigin(), "https://relay-b.example");
+
+  // A's invoke finally resolves late — stale generation, so it is dropped.
+  publishA("https://relay-a.example");
+  assert.equal(getCachedRelayOrigin(), "https://relay-b.example");
+
+  unsubscribe();
+  resetMediaCaches();
+});
+
+test("withDeadline: a never-settling invoke resolves to null at the deadline", async () => {
+  // The poll loop bounds each invoke by the remaining budget so a wedged IPC
+  // bridge (a promise that never settles) can't hang startup past the timeout.
+  const neverSettles = new Promise(() => {});
+  const result = await withDeadline(neverSettles, Date.now() + 20);
+  assert.equal(result, null);
+});
+
+test("withDeadline: a value that settles before the deadline is returned", async () => {
+  const result = await withDeadline(
+    Promise.resolve("http://relay.example"),
+    Date.now() + 1000,
+  );
+  assert.equal(result, "http://relay.example");
+});
+
+test("withDeadline: an already-passed deadline resolves to null without awaiting", async () => {
+  const result = await withDeadline(new Promise(() => {}), Date.now() - 1);
+  assert.equal(result, null);
+});
+
+test("withDeadline: a rejection before the deadline propagates to the caller", async () => {
+  await assert.rejects(
+    withDeadline(Promise.reject(new Error("ipc failed")), Date.now() + 1000),
+    /ipc failed/,
+  );
+});
+
+test("withDeadline: a rejection after the deadline is observed, not unhandled", async () => {
+  // The timeout wins first (deadline ~10ms), then the invoke rejects ~30ms
+  // later. That late rejection must be swallowed by the internal no-op catch,
+  // not surface as an unhandled rejection. Register a listener to prove it.
+  let unhandled;
+  const onUnhandled = (reason) => {
+    unhandled = reason;
+  };
+  process.on("unhandledRejection", onUnhandled);
+  try {
+    const slowReject = new Promise((_resolve, reject) =>
+      setTimeout(() => reject(new Error("late ipc failure")), 30),
+    );
+    const result = await withDeadline(slowReject, Date.now() + 10);
+    assert.equal(result, null);
+    // Give the late rejection time to fire and be (not) reported.
+    await new Promise((r) => setTimeout(r, 40));
+    assert.equal(unhandled, undefined);
+  } finally {
+    process.off("unhandledRejection", onUnhandled);
+  }
+});
diff --git a/desktop/src/shared/lib/mediaUrl.ts b/desktop/src/shared/lib/mediaUrl.ts
index 94e4cc41e..6503d75dd 100644
--- a/desktop/src/shared/lib/mediaUrl.ts
+++ b/desktop/src/shared/lib/mediaUrl.ts
@@ -20,7 +20,7 @@ import { invoke } from "@tauri-apps/api/core";
 // Matches: https://anything.com/media/{64-hex}.{ext}
 // Also matches thumbnails: /media/{64-hex}.thumb.jpg
 const RELAY_MEDIA_RE =
-  /^(?:https?:\/\/[^/]+)\/media\/([\da-f]{64}(?:\.thumb)?\.(?:jpg|png|gif|webp|mp4)(?:\?.*)?)$/;
+  /^(?:https?:\/\/[^/]+)\/media\/([\da-f]{64}(?:\.thumb)?\.(?:jpg|png|gif|webp|mp4|webm|mov)(?:\?.*)?)$/;
 
 /** Cached proxy port — fetched once from the Tauri backend. */
 let cachedPort: number | null = null;
@@ -29,38 +29,150 @@ let portPromise: Promise<number | null> | null = null;
 /** Cached relay origin (e.g. "https://buzz-oss.stage.blox.sqprod.co"). */
 let cachedRelayOrigin: string | null = null;
 
+/**
+ * Generation token for the relay-origin fetch. Bumped on every
+ * `resetMediaCaches` (i.e. workspace switch) so an origin fetch started for
+ * the previous community can never publish its stale origin after the switch:
+ * only a resolution whose generation still matches the current one is applied.
+ */
+let relayOriginGeneration = 0;
+
+/** `useSyncExternalStore` listeners for relay-origin changes. */
+const relayOriginListeners = new Set<() => void>();
+
+function notifyRelayOriginListeners(): void {
+  for (const listener of relayOriginListeners) listener();
+}
+
+/**
+ * Publish a resolved relay origin, but only if `generation` is still current
+ * (the fetch wasn't superseded by a workspace switch). Notifies subscribers
+ * only on an actual snapshot change so `useSyncExternalStore` doesn't churn.
+ */
+function setRelayOrigin(origin: string | null, generation: number): void {
+  if (generation !== relayOriginGeneration) return;
+  if (cachedRelayOrigin === origin) return;
+  cachedRelayOrigin = origin;
+  notifyRelayOriginListeners();
+}
+
+/**
+ * Begin a relay-origin fetch: captures the current generation and returns a
+ * publisher bound to it. The publisher applies the resolved origin only if no
+ * workspace switch (`resetMediaCaches`) has happened in the meantime, so a
+ * fetch started for community A can never publish A's origin after a switch to
+ * community B. Callers invoke the returned function once the origin resolves.
+ */
+export function beginRelayOriginFetch(): (origin: string | null) => void {
+  const generation = relayOriginGeneration;
+  return (origin) => setRelayOrigin(origin, generation);
+}
+
+/**
+ * Subscribe to relay-origin changes. Returns a stable unsubscribe function
+ * (the same closure identity for the life of the subscription), as
+ * `useSyncExternalStore` requires.
+ */
+export function subscribeRelayOrigin(listener: () => void): () => void {
+  relayOriginListeners.add(listener);
+  return () => {
+    relayOriginListeners.delete(listener);
+  };
+}
+
 const POLL_INTERVAL_MS = 100;
 const POLL_TIMEOUT_MS = 5000;
 
+/**
+ * Race `promise` against the remaining time until `deadline`, resolving to
+ * `null` if the deadline passes first. Bounds each poll invoke so a Tauri IPC
+ * call that never settles (bridge wedged, not merely unavailable) cannot hang
+ * the poll loop past its budget. The underlying invoke isn't cancellable, but
+ * abandoning its result is safe here: a late origin resolution is
+ * generation-guarded, and a late port is simply ignored once the loop returns.
+ *
+ * Exported for unit tests (the never-settling case) — it is a self-contained,
+ * generally-useful timeout primitive, not a seam into `fetchProxyPort`.
+ */
+export function withDeadline<T>(
+  promise: Promise<T>,
+  deadline: number,
+): Promise<T | null> {
+  const remaining = deadline - Date.now();
+  // A late rejection (the invoke rejects after the timeout already won the
+  // race) would otherwise surface as an unhandled rejection, so attach a
+  // no-op catch that keeps it observed regardless of which side wins.
+  promise.catch(() => {});
+  if (remaining <= 0) return Promise.resolve(null);
+  return new Promise<T | null>((resolve, reject) => {
+    // Clear the timer once the promise settles so a settled race doesn't leave
+    // a dangling timeout for the rest of the poll budget.
+    const timer = setTimeout(() => resolve(null), remaining);
+    promise.then(
+      (value) => {
+        clearTimeout(timer);
+        resolve(value);
+      },
+      (error) => {
+        clearTimeout(timer);
+        reject(error);
+      },
+    );
+  });
+}
+
 /**
  * Poll `get_media_proxy_port` until we get a non-zero port or timeout.
- * Also fetches the relay HTTP base URL for origin-checking.
+ * Also resolves the relay HTTP base URL for origin-checking.
  * Returns the port, or null if the proxy never came up.
  */
 async function fetchProxyPort(): Promise<number | null> {
-  // Fetch relay origin in parallel — fire-and-forget, no retry needed.
-  if (!cachedRelayOrigin) {
-    invoke<string>("get_relay_http_url")
-      .then((url) => {
-        cachedRelayOrigin = url.replace(/\/+$/, "");
-      })
-      .catch(() => {});
-  }
-
+  // Resolve the relay origin alongside the port, retried inside the same poll
+  // loop. Both invokes can reject early (e.g. Tauri IPC not ready at module
+  // load); the port already retries, and the origin must too — a single
+  // fire-and-forget attempt that fails before the bridge is up would leave the
+  // origin unresolved forever, hiding relay Download eligibility. The publisher
+  // captures the generation at each attempt so a resolution that lands after a
+  // workspace switch is discarded rather than publishing a stale origin.
   const deadline = Date.now() + POLL_TIMEOUT_MS;
   while (Date.now() < deadline) {
-    try {
-      const port = await invoke<number>("get_media_proxy_port");
-      if (port > 0) {
-        cachedPort = port;
-        return port;
+    if (!cachedRelayOrigin) {
+      const publishRelayOrigin = beginRelayOriginFetch();
+      try {
+        const url = await withDeadline(
+          invoke<string>("get_relay_http_url"),
+          deadline,
+        );
+        if (url !== null) publishRelayOrigin(url.replace(/\/+$/, ""));
+      } catch {
+        // invoke failed (e.g. Tauri IPC not ready yet) — keep retrying
       }
-    } catch {
-      // invoke failed (e.g. Tauri IPC not ready yet) — keep retrying
     }
+
+    if (!cachedPort) {
+      try {
+        const port = await withDeadline(
+          invoke<number>("get_media_proxy_port"),
+          deadline,
+        );
+        if (port !== null && port > 0) cachedPort = port;
+      } catch {
+        // invoke failed (e.g. Tauri IPC not ready yet) — keep retrying
+      }
+    }
+
+    // Both readiness results complete independently. Keep polling until BOTH
+    // land: a resolved port lets URL rewriting proceed, but relay-origin
+    // resolution gates Download eligibility, so we must not stop retrying the
+    // origin just because the port is ready (nothing else re-enters this loop
+    // once the port is cached). Each invoke is bounded by the remaining
+    // deadline (`withDeadline`) so a never-settling IPC call can't hang the
+    // loop; every late origin result is generation-guarded.
+    if (cachedPort && cachedRelayOrigin) return cachedPort;
+
     await new Promise((r) => setTimeout(r, POLL_INTERVAL_MS));
   }
-  return null;
+  return cachedPort;
 }
 
 /** Eagerly fetch the port at module load so it's ready by first render. */
@@ -73,11 +185,31 @@ if (typeof window !== "undefined") {
 /**
  * Reset module-level caches so the next render re-fetches the proxy port
  * and relay origin for the new community.
+ *
+ * Bumps the origin generation so any in-flight fetch from the previous
+ * community is discarded on resolution, and notifies subscribers only if the
+ * origin actually changes (a reset from an already-null origin is a no-op for
+ * listeners).
  */
 export function resetMediaCaches(): void {
   cachedPort = null;
   portPromise = null;
-  cachedRelayOrigin = null;
+  relayOriginGeneration += 1;
+  if (cachedRelayOrigin !== null) {
+    cachedRelayOrigin = null;
+    notifyRelayOriginListeners();
+  }
+}
+
+/**
+ * The relay origin (e.g. `https://buzz-oss.stage.blox.sqprod.co`) if it has
+ * been resolved, else `null`. Synchronous best-effort read of the same cache
+ * `rewriteRelayUrl` uses. Callers that need a hard SSRF guarantee must still
+ * rely on the Rust `validate_download_url` gate; this only drives UX (e.g.
+ * whether to offer a Download action that could otherwise only error).
+ */
+export function getCachedRelayOrigin(): string | null {
+  return cachedRelayOrigin;
 }
 
 /**
diff --git a/desktop/src/shared/lib/useRelayOrigin.ts b/desktop/src/shared/lib/useRelayOrigin.ts
new file mode 100644
index 000000000..c29c20d32
--- /dev/null
+++ b/desktop/src/shared/lib/useRelayOrigin.ts
@@ -0,0 +1,24 @@
+import * as React from "react";
+
+import { getCachedRelayOrigin, subscribeRelayOrigin } from "./mediaUrl";
+
+/**
+ * The resolved relay origin, re-rendering when it resolves or changes.
+ *
+ * The origin is fetched asynchronously (see `mediaUrl.ts`) and is commonly
+ * still `null` on a component's first render. Reading it through this store
+ * subscription — rather than a bare synchronous `getCachedRelayOrigin()` —
+ * means download eligibility recomputes the moment the origin resolves and
+ * again on a workspace switch, instead of being frozen at first-render time.
+ *
+ * The server snapshot is `null`: there is no relay origin during SSR/prerender
+ * (no Tauri backend), and callers already treat an unresolved origin as
+ * "not yet downloadable" (fail closed).
+ */
+export function useRelayOrigin(): string | null {
+  return React.useSyncExternalStore(
+    subscribeRelayOrigin,
+    getCachedRelayOrigin,
+    () => null,
+  );
+}
diff --git a/desktop/src/shared/ui/VideoPlayer.tsx b/desktop/src/shared/ui/VideoPlayer.tsx
index 4de5f44ac..908bd8e3f 100644
--- a/desktop/src/shared/ui/VideoPlayer.tsx
+++ b/desktop/src/shared/ui/VideoPlayer.tsx
@@ -13,7 +13,6 @@ import {
   VolumeX,
   X,
 } from "lucide-react";
-
 import { EmojiPicker } from "@/features/custom-emoji/ui/EmojiPicker";
 import { MessageComposer } from "@/features/messages/ui/MessageComposer";
 import type { UserProfileLookup } from "@/features/profile/lib/identity";
@@ -28,6 +27,7 @@ import { Tooltip, TooltipContent, TooltipTrigger } from "@/shared/ui/tooltip";
 import { UserAvatar } from "@/shared/ui/UserAvatar";
 import { Spinner } from "./spinner";
 import { useNaturalVideoAspectRatio } from "./videoAspectRatio";
+import { useVideoContextMenu } from "./useVideoContextMenu";
 import {
   getInlinePlaybackPosition,
   getReviewPlaybackPosition,
@@ -92,6 +92,14 @@ type VideoPlayerProps = {
   durationSeconds?: number;
   reviewKey?: string;
   reviewContext?: VideoReviewContext;
+  /**
+   * Original relay `/media/` URL for the right-click Download action, distinct
+   * from the possibly-proxied `src` the download command's SSRF check rejects.
+   * Omitted for non-relay sources, which hide the Download item.
+   */
+  downloadUrl?: string;
+  /** imeta `filename`, used as the save-dialog name. */
+  filename?: string;
 };
 
 type TimecodedComment = {
@@ -703,6 +711,8 @@ export function VideoPlayer({
   durationSeconds,
   reviewKey,
   reviewContext,
+  downloadUrl,
+  filename,
 }: VideoPlayerProps) {
   const persistedReviewKey = reviewKey ?? src;
   const videoRef = React.useRef<HTMLVideoElement>(null);
@@ -740,6 +750,9 @@ export function VideoPlayer({
     number | null
   >(null);
 
+  const { onContextMenu: onSurfaceContextMenu, menu: videoContextMenu } =
+    useVideoContextMenu(src, downloadUrl, filename);
+
   React.useEffect(() => {
     // The imeta duration seeds the timeline before metadata loads; metadata
     // (set via onLoadedMetadata below) stays authoritative once known.
@@ -988,6 +1001,7 @@ export function VideoPlayer({
           ref={inlineSurfaceRef}
           className="group/video relative isolate max-w-full overflow-hidden rounded-2xl border border-border/70 bg-black"
           style={inlineSurfaceStyle}
+          onContextMenuCapture={onSurfaceContextMenu}
         >
           {/* Cover, not contain: when the surface's max-height clamp breaks
               the aspect match (tall videos), fill the tile and crop instead
@@ -1175,6 +1189,7 @@ export function VideoPlayer({
           </button>
         ) : null}
       </div>
+      {videoContextMenu}
       <VideoReviewDialog
         comments={timecodedComments}
         currentTime={reviewCurrentTime}
diff --git a/desktop/src/shared/ui/markdown.tsx b/desktop/src/shared/ui/markdown.tsx
index f898a5509..b1f9623f3 100644
--- a/desktop/src/shared/ui/markdown.tsx
+++ b/desktop/src/shared/ui/markdown.tsx
@@ -9,6 +9,7 @@ import {
   ZoomOut,
 } from "lucide-react";
 import { AnimatePresence, motion, useReducedMotion } from "motion/react";
+import { openUrl } from "@tauri-apps/plugin-opener";
 import { toast } from "sonner";
 
 import { useAppNavigation } from "@/app/navigation/useAppNavigation";
@@ -22,6 +23,7 @@ import { UserProfilePopover } from "@/features/profile/ui/UserProfilePopover";
 import { invokeTauri } from "@/shared/api/tauri";
 import { useChannelNavigation } from "@/shared/context/ChannelNavigationContext";
 import { cn } from "@/shared/lib/cn";
+import { copyTextToClipboard } from "@/shared/lib/clipboard";
 import {
   extractSupportedLinkPreviews,
   parseSupportedLinkPreview,
@@ -43,11 +45,6 @@ import {
   MENTION_CHIP_PREFIX_CLASS,
   MESSAGE_MARKDOWN_CLASS,
 } from "@/shared/ui/mentionChip";
-import {
-  POPOVER_CUSTOM_ENTER_MOTION_CLASS,
-  POPOVER_SHADOW_STYLE,
-  POPOVER_SURFACE_CLASS,
-} from "@/shared/ui/popoverSurface";
 
 import {
   classifyChildren,
@@ -65,6 +62,12 @@ import {
 import { FileCard } from "./markdown/FileCard";
 import { InlineEmojiPopover } from "./markdown/InlineEmojiPopover";
 import { MarkdownInput } from "./markdown/MarkdownInput";
+import {
+  MediaContextMenu,
+  type MediaContextMenuPosition,
+  useDismissMediaContextMenu,
+} from "./markdown/MediaContextMenu";
+import { isVideoMedia } from "./markdown/mediaEntry";
 import {
   clampImageLightboxZoom,
   type ImageGalleryDirection,
@@ -142,11 +145,6 @@ type WebKitGestureLikeEvent = Event & {
   scale?: number;
 };
 
-type ImageContextMenuPosition = {
-  x: number;
-  y: number;
-};
-
 function getImageLightboxFocusableElements(
   container: HTMLElement,
 ): HTMLElement[] {
@@ -169,69 +167,6 @@ function getImageLightboxFocusableElements(
   );
 }
 
-function useDismissImageContextMenu(isOpen: boolean, onDismiss: () => void) {
-  React.useEffect(() => {
-    if (!isOpen) return;
-    // Defer attaching the dismiss listeners until after the current event
-    // loop turn. The right-click that opens the menu (a `contextmenu` on
-    // mousedown) is often followed by a trailing `click`/`pointerup` on the
-    // same interaction; attaching synchronously lets that trailing event —
-    // and the platform `click` some webviews emit on right-button release —
-    // immediately dismiss the menu, so it only flashes. Deferring guarantees
-    // the opening interaction can never be the one that closes it.
-    let attached = false;
-    const timer = window.setTimeout(() => {
-      attached = true;
-      window.addEventListener("click", onDismiss);
-      window.addEventListener("contextmenu", onDismiss);
-      window.addEventListener("scroll", onDismiss, true);
-    }, 0);
-    return () => {
-      window.clearTimeout(timer);
-      if (attached) {
-        window.removeEventListener("click", onDismiss);
-        window.removeEventListener("contextmenu", onDismiss);
-        window.removeEventListener("scroll", onDismiss, true);
-      }
-    };
-  }, [isOpen, onDismiss]);
-}
-
-function ImageContextMenu({
-  onCopy,
-  onDownload,
-  portalContainer,
-  position,
-}: {
-  onCopy: () => void;
-  onDownload: () => void;
-  portalContainer?: Element;
-  position: ImageContextMenuPosition;
-}) {
-  const itemClass =
-    "flex min-h-9 w-full cursor-default select-none items-center rounded-lg py-2 pl-2 pr-4 text-sm outline-hidden hover:bg-muted/50 hover:text-foreground";
-  return createPortal(
-    <div
-      className={cn(
-        "fixed z-[100] min-w-60 origin-top-left rounded-xl p-1 slide-in-from-top-1",
-        POPOVER_CUSTOM_ENTER_MOTION_CLASS,
-        POPOVER_SURFACE_CLASS,
-      )}
-      data-image-context-menu=""
-      data-image-lightbox-controls=""
-      style={{ ...POPOVER_SHADOW_STYLE, left: position.x, top: position.y }}
-    >
-      <button type="button" className={itemClass} onClick={onCopy}>
-        Copy image
-      </button>
-      <button type="button" className={itemClass} onClick={onDownload}>
-        Download image
-      </button>
-    </div>,
-    portalContainer ?? document.body,
-  );
-}
-
 function ImageZoomOverlay({
   alt,
   galleryIndex = 0,
@@ -287,7 +222,7 @@ function ImageZoomOverlay({
   const [hasEntered, setHasEntered] = React.useState(prefersReducedMotion);
   const [isAdjustingZoom, setIsAdjustingZoom] = React.useState(false);
   const [isGalleryNavigating, setIsGalleryNavigating] = React.useState(false);
-  const [menu, setMenu] = React.useState<ImageContextMenuPosition | null>(null);
+  const [menu, setMenu] = React.useState<MediaContextMenuPosition | null>(null);
   const currentItem = items[currentIndex] ?? items[0];
   const basisBox = React.useMemo(
     () => imageLightboxBasisBoxForItem(currentItem, sourceBox),
@@ -446,7 +381,7 @@ function ImageZoomOverlay({
     navigateGallery(currentIndex + 1);
   }, [currentIndex, navigateGallery]);
 
-  useDismissImageContextMenu(Boolean(menu), closeMenu);
+  useDismissMediaContextMenu(Boolean(menu), closeMenu);
 
   React.useEffect(() => {
     if (prefersReducedMotion) {
@@ -1042,9 +977,15 @@ function ImageZoomOverlay({
         </div>
       </div>
       {menu && canActOnCurrentImage ? (
-        <ImageContextMenu
-          onCopy={handleMenuCopy}
-          onDownload={handleMenuDownload}
+        <MediaContextMenu
+          dataAttributes={[
+            "data-image-context-menu",
+            "data-image-lightbox-controls",
+          ]}
+          items={[
+            { label: "Copy image", onSelect: handleMenuCopy },
+            { label: "Download image", onSelect: handleMenuDownload },
+          ]}
           portalContainer={dialogRef.current ?? undefined}
           position={menu}
         />
@@ -1072,7 +1013,7 @@ function ImageBlock({ alt, dim, resolvedSrc, src, thumbSrc }: ImageBlockProps) {
     sourceScope: Element | null;
   } | null>(null);
   const [isHiddenInSpoiler, setIsHiddenInSpoiler] = React.useState(false);
-  const [menu, setMenu] = React.useState<ImageContextMenuPosition | null>(null);
+  const [menu, setMenu] = React.useState<MediaContextMenuPosition | null>(null);
   const inlineImageRef = React.useRef<HTMLImageElement | null>(null);
   const thumbnailImageRef = React.useRef<HTMLImageElement | null>(null);
   const triggerRef = React.useRef<HTMLButtonElement | null>(null);
@@ -1158,7 +1099,7 @@ function ImageBlock({ alt, dim, resolvedSrc, src, thumbSrc }: ImageBlockProps) {
   }, []);
 
   const closeMenu = React.useCallback(() => setMenu(null), []);
-  useDismissImageContextMenu(Boolean(menu), closeMenu);
+  useDismissMediaContextMenu(Boolean(menu), closeMenu);
 
   const handleContextMenu = (e: React.MouseEvent) => {
     e.preventDefault();
@@ -1279,9 +1220,12 @@ function ImageBlock({ alt, dim, resolvedSrc, src, thumbSrc }: ImageBlockProps) {
         />
       </button>
       {menu && src ? (
-        <ImageContextMenu
-          onCopy={() => handleCopyImage(src)}
-          onDownload={() => handleDownload(src)}
+        <MediaContextMenu
+          dataAttributes={["data-image-context-menu"]}
+          items={[
+            { label: "Copy image", onSelect: () => handleCopyImage(src) },
+            { label: "Download image", onSelect: () => handleDownload(src) },
+          ]}
           position={menu}
         />
       ) : null}
@@ -1328,6 +1272,85 @@ function ImageMosaic({ children }: { children: React.ReactNode[] }) {
   );
 }
 
+/**
+ * An external `[text](href)` link with a custom right-click menu.
+ *
+ * Buzz renders inside a native webview whose default context menu has no
+ * useful link actions, so a plain right-click on a link is a no-op. This adds
+ * an in-app menu with "Open link" (via the OS opener, matching the anchor's
+ * left-click `target="_blank"` behavior) and "Copy link" (the real href, not
+ * the masked display text).
+ */
+function ExternalLinkAnchor({
+  anchorProps,
+  children,
+  href,
+  isLinearLink,
+  label,
+}: {
+  anchorProps: React.ComponentPropsWithoutRef<"a">;
+  children: React.ReactNode;
+  href: string | undefined;
+  isLinearLink: boolean;
+  label: string;
+}) {
+  const [menu, setMenu] = React.useState<MediaContextMenuPosition | null>(null);
+  const closeMenu = React.useCallback(() => setMenu(null), []);
+  useDismissMediaContextMenu(Boolean(menu), closeMenu);
+
+  const anchor = (
+    <a
+      {...anchorProps}
+      className={cn(
+        "font-medium underline underline-offset-4 transition-colors",
+        isLinearLink ? "linear-link" : "text-primary hover:text-primary/80",
+      )}
+      href={href}
+      onContextMenuCapture={(event) => {
+        if (!href) return;
+        event.preventDefault();
+        setMenu({ x: event.clientX, y: event.clientY });
+      }}
+      rel="noreferrer"
+      target="_blank"
+    >
+      {children}
+    </a>
+  );
+
+  return (
+    <>
+      <MaskedLinkTooltip disabled={isLinearLink} href={href} label={label}>
+        {anchor}
+      </MaskedLinkTooltip>
+      {menu && href ? (
+        <MediaContextMenu
+          dataAttributes={["data-link-context-menu"]}
+          items={[
+            {
+              label: "Open link",
+              onSelect: () => {
+                closeMenu();
+                void openUrl(href).catch(() => {
+                  toast.error("Failed to open link");
+                });
+              },
+            },
+            {
+              label: "Copy link",
+              onSelect: () => {
+                closeMenu();
+                copyTextToClipboard(href, "Link copied to clipboard");
+              },
+            },
+          ]}
+          position={menu}
+        />
+      ) : null}
+    </>
+  );
+}
+
 function createMarkdownComponents(
   interactive = true,
   mediaInset = false,
@@ -1445,25 +1468,15 @@ function createMarkdownComponents(
     const supportedLinkPreview = href ? parseSupportedLinkPreview(href) : null;
     const isLinearLink = supportedLinkPreview?.kind === "linear-issue";
 
-    const anchor = (
-      <a
-        {...props}
-        className={cn(
-          "font-medium underline underline-offset-4 transition-colors",
-          isLinearLink ? "linear-link" : "text-primary hover:text-primary/80",
-        )}
+    return (
+      <ExternalLinkAnchor
+        anchorProps={props}
         href={href}
-        rel="noreferrer"
-        target="_blank"
+        isLinearLink={isLinearLink}
+        label={label}
       >
         {children}
-      </a>
-    );
-
-    return (
-      <MaskedLinkTooltip disabled={isLinearLink} href={href} label={label}>
-        {anchor}
-      </MaskedLinkTooltip>
+      </ExternalLinkAnchor>
     );
   }
 
@@ -1556,16 +1569,15 @@ function createMarkdownComponents(
     hr: () => <hr className="border-border/80" />,
     img: function MarkdownImage({ alt, src }) {
       const { imetaByUrl } = useMarkdownRuntime();
-      const resolvedSrc = src ? rewriteRelayUrl(src) : src;
+      const entry = src ? imetaByUrl?.get(src) : undefined;
+      const isVideo = src ? isVideoMedia(src, entry?.m) : false;
       if (!interactive) {
-        const fallbackLabel = resolvedSrc?.endsWith(".mp4")
-          ? "Video attachment"
-          : "Image attachment";
+        const fallbackLabel = isVideo ? "Video attachment" : "Image attachment";
         return <span>{alt?.trim() || fallbackLabel}</span>;
       }
 
-      if (resolvedSrc?.endsWith(".mp4")) {
-        const entry = src ? imetaByUrl?.get(src) : undefined;
+      const resolvedSrc = src ? rewriteRelayUrl(src) : src;
+      if (isVideo && src && resolvedSrc) {
         return (
           <span
             className={cn(
@@ -1583,7 +1595,6 @@ function createMarkdownComponents(
           </span>
         );
       }
-      const entry = src ? imetaByUrl?.get(src) : undefined;
       return (
         <span data-block-media="" className="block min-w-0 max-w-full">
           <ImageBlock
diff --git a/desktop/src/shared/ui/markdown/MarkdownVideoPlayer.tsx b/desktop/src/shared/ui/markdown/MarkdownVideoPlayer.tsx
index f16949954..1bb5a35a1 100644
--- a/desktop/src/shared/ui/markdown/MarkdownVideoPlayer.tsx
+++ b/desktop/src/shared/ui/markdown/MarkdownVideoPlayer.tsx
@@ -1,8 +1,10 @@
 import * as React from "react";
 
 import { rewriteRelayUrl } from "@/shared/lib/mediaUrl";
+import { useRelayOrigin } from "@/shared/lib/useRelayOrigin";
 
 import { VideoPlayer, type VideoReviewContext } from "../VideoPlayer";
+import { isRelayDownloadable } from "./mediaEntry";
 import type { ImetaEntry } from "./types";
 import { aspectRatioFromDim } from "./utils";
 
@@ -30,6 +32,17 @@ export function MarkdownVideoPlayer({
   src?: string;
 }) {
   const videoReviewContext = React.useContext(VideoReviewMarkdownContext);
+  // Download eligibility is independent of rendering as a video: only a
+  // relay-hosted `/media/` URL can pass the native `download_file` SSRF gate,
+  // so an external video renders and offers Copy Link but omits Download.
+  //
+  // Read the relay origin reactively: it resolves asynchronously and is
+  // commonly still null on first render, so a synchronous read would freeze
+  // eligibility (Download stays hidden even for a genuine relay URL). The
+  // subscription re-renders when the origin resolves and on workspace switch.
+  const relayOrigin = useRelayOrigin();
+  const downloadUrl =
+    src && isRelayDownloadable(src, relayOrigin ?? undefined) ? src : undefined;
   // Look up poster frame from imeta tags (NIP-71 `image` field).
   // Fall back to `thumb` for compatibility with older events.
   const posterUrl = entry?.image ?? entry?.thumb;
@@ -54,6 +67,8 @@ export function MarkdownVideoPlayer({
       durationSeconds={entry?.duration}
       reviewKey={src ?? resolvedSrc}
       reviewContext={resolvedReviewContext}
+      downloadUrl={downloadUrl}
+      filename={entry?.filename}
     />
   );
 }
diff --git a/desktop/src/shared/ui/markdown/MediaContextMenu.tsx b/desktop/src/shared/ui/markdown/MediaContextMenu.tsx
new file mode 100644
index 000000000..3458dad03
--- /dev/null
+++ b/desktop/src/shared/ui/markdown/MediaContextMenu.tsx
@@ -0,0 +1,111 @@
+import * as React from "react";
+import { createPortal } from "react-dom";
+
+import { cn } from "@/shared/lib/cn";
+import {
+  POPOVER_CUSTOM_ENTER_MOTION_CLASS,
+  POPOVER_SHADOW_STYLE,
+  POPOVER_SURFACE_CLASS,
+} from "@/shared/ui/popoverSurface";
+
+export type MediaContextMenuPosition = {
+  x: number;
+  y: number;
+};
+
+export type MediaContextMenuItem = {
+  label: string;
+  onSelect: () => void;
+};
+
+/**
+ * Dismiss listeners for a custom right-click menu.
+ *
+ * Deferring attachment until after the current event-loop turn matters: the
+ * right-click that opens the menu (a `contextmenu` on mousedown) is often
+ * followed by a trailing `click`/`pointerup` on the same interaction — and
+ * some webviews emit a platform `click` on right-button release. Attaching
+ * synchronously lets that trailing event immediately dismiss the menu, so it
+ * only flashes. Deferring guarantees the opening interaction can never be the
+ * one that closes it.
+ */
+export function useDismissMediaContextMenu(
+  isOpen: boolean,
+  onDismiss: () => void,
+) {
+  React.useEffect(() => {
+    if (!isOpen) return;
+    let attached = false;
+    const timer = window.setTimeout(() => {
+      attached = true;
+      window.addEventListener("click", onDismiss);
+      window.addEventListener("contextmenu", onDismiss);
+      window.addEventListener("scroll", onDismiss, true);
+    }, 0);
+    return () => {
+      window.clearTimeout(timer);
+      if (attached) {
+        window.removeEventListener("click", onDismiss);
+        window.removeEventListener("contextmenu", onDismiss);
+        window.removeEventListener("scroll", onDismiss, true);
+      }
+    };
+  }, [isOpen, onDismiss]);
+}
+
+/**
+ * A small right-click menu for media and links, positioned at the pointer.
+ *
+ * Rendered into `portalContainer` (defaults to `document.body`) so it escapes
+ * overflow-clipped ancestors. Callers own open/close state and must pair this
+ * with `useDismissMediaContextMenu`.
+ */
+export function MediaContextMenu({
+  dataAttributes,
+  items,
+  portalContainer,
+  position,
+}: {
+  /**
+   * Optional empty-valued data attributes (e.g. `["data-image-context-menu"]`)
+   * set on the menu root so e2e locators can target a specific menu variant —
+   * image, link, and video menus pass distinct attributes so tests never alias
+   * one surface for another. The image variant also passes
+   * `data-image-lightbox-controls` so the in-lightbox dismiss guard treats its
+   * own menu as an interior control. All menus additionally carry the shared
+   * generic `data-media-context-menu` marker.
+   */
+  dataAttributes?: string[];
+  items: MediaContextMenuItem[];
+  portalContainer?: Element;
+  position: MediaContextMenuPosition;
+}) {
+  const itemClass =
+    "flex min-h-9 w-full cursor-default select-none items-center rounded-lg py-2 pl-2 pr-4 text-sm outline-hidden hover:bg-muted/50 hover:text-foreground";
+  return createPortal(
+    <div
+      className={cn(
+        "fixed z-[100] min-w-60 origin-top-left rounded-xl p-1 slide-in-from-top-1",
+        POPOVER_CUSTOM_ENTER_MOTION_CLASS,
+        POPOVER_SURFACE_CLASS,
+      )}
+      data-media-context-menu=""
+      {...Object.fromEntries(
+        (dataAttributes ?? []).map((attribute) => [attribute, ""]),
+      )}
+      style={{ ...POPOVER_SHADOW_STYLE, left: position.x, top: position.y }}
+    >
+      {items.map((item) => (
+        <button
+          className={itemClass}
+          key={item.label}
+          onClick={item.onSelect}
+          type="button"
+        >
+          {item.label}
+        </button>
+      ))}
+    </div>,
+    portalContainer ?? document.body,
+  );
+}
diff --git a/desktop/src/shared/ui/markdown/mediaEntry.test.mjs b/desktop/src/shared/ui/markdown/mediaEntry.test.mjs
new file mode 100644
index 000000000..bbd10898b
--- /dev/null
+++ b/desktop/src/shared/ui/markdown/mediaEntry.test.mjs
@@ -0,0 +1,111 @@
+import assert from "node:assert/strict";
+import { test } from "node:test";
+
+import { isRelayDownloadable, isVideoMedia } from "./mediaEntry.ts";
+
+const RELAY = "https://relay.example.com";
+const relayUrl = (name) => `${RELAY}/media/${name}`;
+
+// ── isVideoMedia: MIME-first classification ──────────────────────────────
+
+test("isVideoMedia: video/* MIME classifies as video regardless of extension", () => {
+  assert.equal(isVideoMedia(relayUrl("abc"), "video/mp4"), true);
+  assert.equal(isVideoMedia(relayUrl("abc.jpg"), "video/webm"), true);
+});
+
+test("isVideoMedia: MIME wins for an extensionless relay URL", () => {
+  // The relay path is a content hash with no extension; MIME is the only signal.
+  assert.equal(isVideoMedia(relayUrl("deadbeef"), "video/quicktime"), true);
+});
+
+test("isVideoMedia: uppercase MIME still matches", () => {
+  assert.equal(isVideoMedia(relayUrl("abc"), "VIDEO/MP4"), true);
+});
+
+test("isVideoMedia: image MIME is not a video", () => {
+  assert.equal(isVideoMedia(relayUrl("abc.mp4"), "image/png"), false);
+});
+
+// ── isVideoMedia: legacy extension fallback (no MIME) ─────────────────────
+
+test("isVideoMedia: legacy mp4/webm/mov extensions classify as video", () => {
+  assert.equal(isVideoMedia(relayUrl("abc.mp4")), true);
+  assert.equal(isVideoMedia(relayUrl("abc.webm")), true);
+  assert.equal(isVideoMedia(relayUrl("abc.mov")), true);
+});
+
+test("isVideoMedia: uppercase extension classifies as video", () => {
+  assert.equal(isVideoMedia(relayUrl("abc.MP4")), true);
+  assert.equal(isVideoMedia(relayUrl("abc.WebM")), true);
+});
+
+test("isVideoMedia: extension with a query string still classifies", () => {
+  assert.equal(isVideoMedia(relayUrl("abc.mp4?v=2")), true);
+  assert.equal(isVideoMedia(relayUrl("abc.webm#t=10")), true);
+});
+
+test("isVideoMedia: image extensions are not videos", () => {
+  assert.equal(isVideoMedia(relayUrl("abc.jpg")), false);
+  assert.equal(isVideoMedia(relayUrl("abc.png")), false);
+});
+
+test("isVideoMedia: an extension substring is not enough", () => {
+  // "notmp4" must not match "mp4" — only the real trailing extension counts.
+  assert.equal(isVideoMedia(relayUrl("clip.notmp4")), false);
+});
+
+test("isVideoMedia: malformed / extensionless URL without MIME is not a video", () => {
+  assert.equal(isVideoMedia("not a url"), false);
+  assert.equal(isVideoMedia(relayUrl("deadbeef")), false);
+});
+
+// ── isRelayDownloadable: eligibility, independent of render kind ──────────
+
+test("isRelayDownloadable: relay /media/ URL on the resolved origin is eligible", () => {
+  assert.equal(isRelayDownloadable(relayUrl("abc.mp4"), RELAY), true);
+});
+
+test("isRelayDownloadable: off-relay URL is not eligible", () => {
+  assert.equal(
+    isRelayDownloadable("https://evil.example.com/media/abc.mp4", RELAY),
+    false,
+  );
+});
+
+test("isRelayDownloadable: non-/media/ path on the relay is not eligible", () => {
+  assert.equal(isRelayDownloadable(`${RELAY}/other/abc.mp4`, RELAY), false);
+});
+
+test("isRelayDownloadable: malformed URL is not eligible", () => {
+  assert.equal(isRelayDownloadable("not a url", RELAY), false);
+});
+
+test("isRelayDownloadable: unresolved origin fails closed (no Download offered)", () => {
+  // Before the relay origin resolves we can't distinguish a relay /media/ URL
+  // from an off-relay one, so eligibility fails closed — offering Download for
+  // an off-relay URL would only error, and the Rust gate rejects it anyway.
+  // Callers read the origin from a reactive source so eligibility recomputes
+  // once it resolves (see the transition cases below).
+  assert.equal(isRelayDownloadable(relayUrl("abc.mp4")), false);
+  assert.equal(isRelayDownloadable(relayUrl("abc.mp4"), undefined), false);
+  assert.equal(
+    isRelayDownloadable("https://evil.example.com/media/abc.mp4"),
+    false,
+  );
+});
+
+test("isRelayDownloadable: unresolved → relay origin makes a relay URL eligible", () => {
+  const src = relayUrl("abc.mp4");
+  // First render: origin unresolved → Download hidden.
+  assert.equal(isRelayDownloadable(src, undefined), false);
+  // Origin resolves to the relay → the same URL becomes eligible.
+  assert.equal(isRelayDownloadable(src, RELAY), true);
+});
+
+test("isRelayDownloadable: unresolved → off-relay origin keeps an external URL hidden", () => {
+  const src = "https://evil.example.com/media/abc.mp4";
+  // First render: origin unresolved → hidden.
+  assert.equal(isRelayDownloadable(src, undefined), false);
+  // Origin resolves to a different (relay) origin → still hidden.
+  assert.equal(isRelayDownloadable(src, RELAY), false);
+});
diff --git a/desktop/src/shared/ui/markdown/mediaEntry.ts b/desktop/src/shared/ui/markdown/mediaEntry.ts
new file mode 100644
index 000000000..8cc0160de
--- /dev/null
+++ b/desktop/src/shared/ui/markdown/mediaEntry.ts
@@ -0,0 +1,77 @@
+/**
+ * Pure classification of a markdown media URL: whether it should render as a
+ * video, and whether it can be downloaded — two related but independent
+ * questions.
+ *
+ * `isVideoMedia` decides the render path (video player vs. image block).
+ * `isRelayDownloadable` decides download eligibility, which is separate: an
+ * off-relay video still renders as a video and can be Copy-Link'd, it just
+ * can't be downloaded (the Rust `validate_download_url` SSRF gate accepts only
+ * relay `/media/` origins, so offering Download for an external URL would only
+ * produce an error).
+ *
+ * Kept DOM-free so the branch logic is unit-testable without a webview.
+ */
+
+/** Legacy video extensions, used only when an imeta MIME type is absent. */
+const VIDEO_EXTENSIONS = ["mp4", "webm", "mov"] as const;
+
+/** The lowercased path extension of a URL, ignoring query strings and hashes. */
+function urlPathExtension(src: string): string | undefined {
+  let pathname: string;
+  try {
+    pathname = new URL(src).pathname;
+  } catch {
+    // Relative or malformed URL — strip query/hash by hand.
+    pathname = src.split(/[?#]/, 1)[0];
+  }
+  const lastDot = pathname.lastIndexOf(".");
+  if (lastDot < 0 || lastDot === pathname.length - 1) return undefined;
+  return pathname.slice(lastDot + 1).toLowerCase();
+}
+
+/**
+ * Whether `src` should render as a video.
+ *
+ * The imeta MIME type is authoritative when present (uploads tag every
+ * attachment with `m`): a `video/*` MIME renders as video, and any other MIME
+ * renders as an image regardless of the URL extension. Only when the MIME is
+ * absent (legacy events that predate the tag) do we fall back to a path
+ * extension check.
+ */
+export function isVideoMedia(src: string, imetaMime?: string): boolean {
+  if (imetaMime) return imetaMime.toLowerCase().startsWith("video/");
+  const ext = urlPathExtension(src);
+  return (
+    ext !== undefined && (VIDEO_EXTENSIONS as readonly string[]).includes(ext)
+  );
+}
+
+/**
+ * Whether `src` is a relay-hosted `/media/` URL on `relayOrigin`.
+ *
+ * This mirrors the Rust `validate_download_url` origin+path check for UX
+ * purposes only — the Rust gate remains the authoritative SSRF boundary.
+ *
+ * Fails closed when the relay origin has not resolved yet (`relayOrigin`
+ * absent): an unresolved origin means we can't distinguish a relay `/media/`
+ * URL from an off-relay one, so we do NOT offer Download (offering it for an
+ * off-relay URL would only produce an error, and the Rust gate would reject
+ * it anyway). Callers must read `relayOrigin` from a reactive source
+ * (`useRelayOrigin`) so eligibility recomputes — and Download appears for a
+ * genuine relay URL — the moment the origin resolves.
+ */
+export function isRelayDownloadable(
+  src: string,
+  relayOrigin?: string,
+): boolean {
+  if (!relayOrigin) return false;
+  let parsed: URL;
+  try {
+    parsed = new URL(src);
+  } catch {
+    return false;
+  }
+  if (!parsed.pathname.startsWith("/media/")) return false;
+  return parsed.origin === relayOrigin;
+}
diff --git a/desktop/src/shared/ui/useVideoContextMenu.tsx b/desktop/src/shared/ui/useVideoContextMenu.tsx
new file mode 100644
index 000000000..ec6c5791f
--- /dev/null
+++ b/desktop/src/shared/ui/useVideoContextMenu.tsx
@@ -0,0 +1,83 @@
+import * as React from "react";
+
+import { invokeTauri } from "@/shared/api/tauri";
+import { copyTextToClipboard } from "@/shared/lib/clipboard";
+import {
+  MediaContextMenu,
+  type MediaContextMenuItem,
+  type MediaContextMenuPosition,
+  useDismissMediaContextMenu,
+} from "@/shared/ui/markdown/MediaContextMenu";
+import { resolveVideoDownloadFilename } from "@/shared/ui/videoDownload";
+import { toast } from "sonner";
+
+type UseVideoContextMenu = {
+  /** `onContextMenuCapture` handler for the inline video surface. */
+  onContextMenu: (event: React.MouseEvent) => void;
+  /** The positioned menu element while open, or `null`. */
+  menu: React.ReactNode;
+};
+
+/**
+ * Owns the inline video right-click menu: open/close state, the pointer-anchor
+ * handler, and the Download/Copy actions. Kept out of `VideoPlayer` so that
+ * large component stays focused on playback, and out of the pure
+ * `videoDownload.ts` helpers so they keep their DOM-free, Node-testable shape.
+ *
+ * `downloadUrl` is the original relay `/media/` URL (distinct from a rewritten
+ * proxy `src`); when absent the menu omits Download and offers only Copy link,
+ * so a non-relay video — which the download command's SSRF gate would reject —
+ * never surfaces an action that could only error.
+ */
+export function useVideoContextMenu(
+  src: string,
+  downloadUrl?: string,
+  filename?: string,
+): UseVideoContextMenu {
+  const [position, setPosition] =
+    React.useState<MediaContextMenuPosition | null>(null);
+  const close = React.useCallback(() => setPosition(null), []);
+  useDismissMediaContextMenu(Boolean(position), close);
+
+  const onContextMenu = React.useCallback((event: React.MouseEvent) => {
+    event.preventDefault();
+    setPosition({ x: event.clientX, y: event.clientY });
+  }, []);
+
+  const items = React.useMemo<MediaContextMenuItem[]>(() => {
+    const entries: MediaContextMenuItem[] = [];
+    if (downloadUrl) {
+      entries.push({
+        label: "Download video",
+        onSelect: () => {
+          close();
+          invokeTauri("download_file", {
+            url: downloadUrl,
+            filename: resolveVideoDownloadFilename(filename),
+          }).catch((err: unknown) => {
+            toast.error(err instanceof Error ? err.message : "Download failed");
+          });
+        },
+      });
+    }
+    entries.push({
+      label: "Copy link",
+      onSelect: () => {
+        close();
+        copyTextToClipboard(downloadUrl ?? src, "Link copied to clipboard");
+      },
+    });
+    return entries;
+  }, [close, downloadUrl, filename, src]);
+
+  return {
+    onContextMenu,
+    menu: position ? (
+      <MediaContextMenu
+        dataAttributes={["data-video-context-menu"]}
+        items={items}
+        position={position}
+      />
+    ) : null,
+  };
+}
diff --git a/desktop/src/shared/ui/videoDownload.test.mjs b/desktop/src/shared/ui/videoDownload.test.mjs
new file mode 100644
index 000000000..cc7dd4fee
--- /dev/null
+++ b/desktop/src/shared/ui/videoDownload.test.mjs
@@ -0,0 +1,24 @@
+import assert from "node:assert/strict";
+import { test } from "node:test";
+
+import {
+  DEFAULT_VIDEO_FILENAME,
+  resolveVideoDownloadFilename,
+} from "./videoDownload.ts";
+
+test("resolveVideoDownloadFilename: keeps a real imeta filename", () => {
+  assert.equal(resolveVideoDownloadFilename("clip.webm"), "clip.webm");
+});
+
+test("resolveVideoDownloadFilename: trims surrounding whitespace", () => {
+  assert.equal(resolveVideoDownloadFilename("  demo.mp4  "), "demo.mp4");
+});
+
+test("resolveVideoDownloadFilename: falls back when undefined", () => {
+  assert.equal(resolveVideoDownloadFilename(undefined), DEFAULT_VIDEO_FILENAME);
+});
+
+test("resolveVideoDownloadFilename: falls back when empty / whitespace-only", () => {
+  assert.equal(resolveVideoDownloadFilename(""), DEFAULT_VIDEO_FILENAME);
+  assert.equal(resolveVideoDownloadFilename("   "), DEFAULT_VIDEO_FILENAME);
+});
diff --git a/desktop/src/shared/ui/videoDownload.ts b/desktop/src/shared/ui/videoDownload.ts
new file mode 100644
index 000000000..d45af0f31
--- /dev/null
+++ b/desktop/src/shared/ui/videoDownload.ts
@@ -0,0 +1,20 @@
+/**
+ * Pure helpers for the inline video right-click menu, kept out of the
+ * component so the branch logic is unit-testable without a DOM.
+ */
+
+/** Fallback save-dialog name when the imeta `filename` field is absent. */
+export const DEFAULT_VIDEO_FILENAME = "video.mp4";
+
+/**
+ * The suggested filename passed to the native `download_file` command.
+ *
+ * The relay only stores a content hash in the URL path, so the imeta
+ * `filename` is the only human-readable name we have. When it is missing we
+ * fall back to a generic `.mp4` name (the backend re-derives the real
+ * extension defensively from this value).
+ */
+export function resolveVideoDownloadFilename(filename?: string): string {
+  const trimmed = filename?.trim();
+  return trimmed ? trimmed : DEFAULT_VIDEO_FILENAME;
+}
diff --git a/desktop/tests/e2e/image-attachment-gallery.spec.ts b/desktop/tests/e2e/image-attachment-gallery.spec.ts
index cc7490739..d5c81ceed 100644
--- a/desktop/tests/e2e/image-attachment-gallery.spec.ts
+++ b/desktop/tests/e2e/image-attachment-gallery.spec.ts
@@ -770,6 +770,14 @@ test("right-click image shows Copy image and invokes copy command", async ({
     page.getByRole("button", { name: "Download image" }),
   ).toBeVisible();
 
+  // The image menu carries the shared generic marker plus its own image-
+  // specific attribute, and never the link/video attributes — so e2e locators
+  // can target one surface without aliasing another.
+  await expect(page.locator("[data-media-context-menu]")).toBeVisible();
+  await expect(page.locator("[data-image-context-menu]")).toBeVisible();
+  await expect(page.locator("[data-link-context-menu]")).toHaveCount(0);
+  await expect(page.locator("[data-video-context-menu]")).toHaveCount(0);
+
   await copyButton.click();
 
   await expect
diff --git a/desktop/tests/e2e/video-attachment.spec.ts b/desktop/tests/e2e/video-attachment.spec.ts
index 36c5dbdd6..8f4bb0aa4 100644
--- a/desktop/tests/e2e/video-attachment.spec.ts
+++ b/desktop/tests/e2e/video-attachment.spec.ts
@@ -9,6 +9,14 @@ const PORTRAIT_VIDEO_SHA = "c".repeat(64);
 const PORTRAIT_VIDEO_URL = `http://localhost:3000/media/${PORTRAIT_VIDEO_SHA}.mp4`;
 const CONSTRAINED_LANDSCAPE_VIDEO_SHA = "d".repeat(64);
 const CONSTRAINED_LANDSCAPE_VIDEO_URL = `http://localhost:3000/media/${CONSTRAINED_LANDSCAPE_VIDEO_SHA}.mp4`;
+// Distinct-selector context-menu probes. The relay video is on the resolved
+// relay origin (localhost:3000) so it is Download-eligible once the origin
+// resolves; the off-relay video shares an identical /media/ path shape on a
+// different origin, so it renders and offers Copy link but never Download.
+const MENU_RELAY_VIDEO_SHA = "e".repeat(64);
+const MENU_RELAY_VIDEO_URL = `http://localhost:3000/media/${MENU_RELAY_VIDEO_SHA}.mp4`;
+const MENU_OFF_RELAY_VIDEO_SHA = "f".repeat(64);
+const MENU_OFF_RELAY_VIDEO_URL = `https://cdn.example.com/media/${MENU_OFF_RELAY_VIDEO_SHA}.mp4`;
 const VIDEO_REVIEW_NEUTRAL_ACCENT = "neutral";
 const VIDEO_REVIEW_LIGHT_THEME = "catppuccin-latte";
 // The fresh-profile default is the Buzz theme, which pins the neutral accent
@@ -892,3 +900,140 @@ test("dark accent uses a contrast-safe review foreground", async ({ page }) => {
     reviewDialog.getByTestId("video-review-comment-timecode").first(),
   ).toHaveCSS("color", VIDEO_REVIEW_INDIGO_FOREGROUND_RGB);
 });
+
+// Emit a video message with the imeta the renderer needs to pick the video
+// player and, for the relay case, a resolvable download URL.
+function emitVideoMessage(
+  page: Page,
+  { url, sha, filename }: { url: string; sha: string; filename: string },
+) {
+  return emitMockMessage(page, "general", `![video](${url})`, {
+    extraTags: [
+      [
+        "imeta",
+        `url ${url}`,
+        "m video/mp4",
+        `x ${sha}`,
+        "size 987654",
+        "dim 160x80",
+        "duration 12.5",
+        `image ${POSTER_DATA_URL}`,
+        `filename ${filename}`,
+      ],
+    ],
+  });
+}
+
+test("right-click menus expose distinct selectors for links, relay video, and off-relay video", async ({
+  page,
+}) => {
+  await installVideoReviewHarness(page);
+
+  await page.goto("/");
+  await page.getByTestId("channel-general").click();
+  await expect(page.getByTestId("chat-title")).toHaveText("general");
+  await waitForMockLiveSubscription(page, "general");
+
+  // ── Link menu: Open link + Copy link, never image/video attributes ────────
+  await emitMockMessage(
+    page,
+    "general",
+    "Docs at https://example.com/handbook",
+  );
+  const link = page.getByRole("link", { name: "https://example.com/handbook" });
+  await expect(link).toBeVisible();
+  await link.scrollIntoViewIfNeeded();
+  // Fire a real bubbling `contextmenu` MouseEvent on the anchor rather than
+  // `.click({ button: "right" })`: the link is wrapped in a hover tooltip and a
+  // positional right-click can land on the tooltip layer (or merely select the
+  // text) without reaching the anchor's React `onContextMenuCapture`. An
+  // element-targeted bubbling event drives the capture handler deterministically.
+  await link.evaluate((el) =>
+    el.dispatchEvent(
+      new MouseEvent("contextmenu", { bubbles: true, cancelable: true }),
+    ),
+  );
+
+  const linkMenu = page.locator("[data-link-context-menu]");
+  await expect(linkMenu).toBeVisible();
+  await expect(page.locator("[data-media-context-menu]")).toBeVisible();
+  await expect(
+    linkMenu.getByRole("button", { name: "Open link" }),
+  ).toBeVisible();
+  await expect(
+    linkMenu.getByRole("button", { name: "Copy link" }),
+  ).toBeVisible();
+  await expect(page.locator("[data-image-context-menu]")).toHaveCount(0);
+  await expect(page.locator("[data-video-context-menu]")).toHaveCount(0);
+  // Dismiss the menu before the next probe: the menu closes on any click.
+  await page.getByTestId("chat-title").click();
+  await expect(linkMenu).toHaveCount(0);
+
+  // ── Relay video menu: Download video + Copy link, appearing only once the
+  // relay origin resolves (the reactivity fix) ─────────────────────────────
+  await emitVideoMessage(page, {
+    url: MENU_RELAY_VIDEO_URL,
+    sha: MENU_RELAY_VIDEO_SHA,
+    filename: "relay-clip.mp4",
+  });
+  const relayPlayer = page.getByTestId("video-player").last();
+  await expect(relayPlayer).toBeVisible();
+  // Right-click the player surface. `force` skips the actionability guard: the
+  // Play-button overlay sits above the video, but the contextmenu event still
+  // capture-bubbles to the surface handler that opens the menu.
+  await relayPlayer.click({ button: "right", force: true });
+
+  const videoMenu = page.locator("[data-video-context-menu]");
+  await expect(videoMenu).toBeVisible();
+  await expect(page.locator("[data-media-context-menu]")).toBeVisible();
+  // Download eligibility is reactive: the relay origin resolves asynchronously
+  // (commonly after first render), and when it does the already-open menu
+  // recomputes to reveal Download — no re-navigation or menu re-open.
+  await expect(
+    videoMenu.getByRole("button", { name: "Download video" }),
+  ).toBeVisible();
+  await expect(
+    videoMenu.getByRole("button", { name: "Copy link" }),
+  ).toBeVisible();
+  await expect(page.locator("[data-image-context-menu]")).toHaveCount(0);
+  await expect(page.locator("[data-link-context-menu]")).toHaveCount(0);
+
+  // The Download action drives the native download_file command.
+  await videoMenu.getByRole("button", { name: "Download video" }).click();
+  await expect
+    .poll(() =>
+      page.evaluate(
+        () =>
+          (window as Window & { __BUZZ_E2E_COMMANDS__?: string[] })
+            .__BUZZ_E2E_COMMANDS__ ?? [],
+      ),
+    )
+    .toContain("download_file");
+
+  // Dismiss the relay menu before the off-relay probe so `[data-video-context
+  // -menu]` refers unambiguously to the off-relay video's menu below. The menu
+  // closes on any click.
+  await page.getByTestId("chat-title").click();
+  await expect(page.locator("[data-video-context-menu]")).toHaveCount(0);
+
+  // ── Off-relay video control: renders and offers Copy link, never Download ─
+  await emitVideoMessage(page, {
+    url: MENU_OFF_RELAY_VIDEO_URL,
+    sha: MENU_OFF_RELAY_VIDEO_SHA,
+    filename: "external-clip.mp4",
+  });
+  const offRelayPlayer = page.getByTestId("video-player").last();
+  await expect(offRelayPlayer).toBeVisible();
+  await offRelayPlayer.click({ button: "right", force: true });
+
+  const offRelayMenu = page.locator("[data-video-context-menu]");
+  await expect(offRelayMenu).toBeVisible();
+  await expect(
+    offRelayMenu.getByRole("button", { name: "Copy link" }),
+  ).toBeVisible();
+  // An off-relay video would fail the download command's SSRF gate, so the
+  // menu must never offer Download for it.
+  await expect(
+    offRelayMenu.getByRole("button", { name: "Download video" }),
+  ).toHaveCount(0);
+});