diff --git a/desktop/src/shared/ui/link-preview-attachment.tsx b/desktop/src/shared/ui/link-preview-attachment.tsx
index bb8fe352b..c125f5898 100644
--- a/desktop/src/shared/ui/link-preview-attachment.tsx
+++ b/desktop/src/shared/ui/link-preview-attachment.tsx
@@ -1,22 +1,39 @@
 import type { ResolvedLinkPreview } from "@/shared/lib/useResolvedLinkPreviews";
 import { useLinkPreviewStyle } from "@/shared/lib/linkPreviewStylePreference";
 import { CompactLinkPreviewAttachment } from "@/shared/ui/compact-link-preview-attachment";
-import { RichLinkPreviewAttachment } from "@/shared/ui/rich-link-preview-attachment";
+import {
+  type LinkPreviewImageLightboxComponent,
+  RichLinkPreviewAttachment,
+} from "@/shared/ui/rich-link-preview-attachment";
 
 export function LinkPreviewAttachment({
   className,
+  ImageLightbox,
   onRemove,
   preview,
 }: {
   className?: string;
+  ImageLightbox: LinkPreviewImageLightboxComponent;
   onRemove?: () => void;
   preview: ResolvedLinkPreview;
 }) {
   const style = useLinkPreviewStyle();
-  const Preview =
-    style === "rich" ? RichLinkPreviewAttachment : CompactLinkPreviewAttachment;
+  if (style === "rich") {
+    return (
+      <RichLinkPreviewAttachment
+        className={className}
+        ImageLightbox={ImageLightbox}
+        onRemove={onRemove}
+        preview={preview}
+      />
+    );
+  }
 
   return (
-    <Preview className={className} onRemove={onRemove} preview={preview} />
+    <CompactLinkPreviewAttachment
+      className={className}
+      onRemove={onRemove}
+      preview={preview}
+    />
   );
 }
diff --git a/desktop/src/shared/ui/link-preview-list.tsx b/desktop/src/shared/ui/link-preview-list.tsx
index dd95a49a7..2c36e7596 100644
--- a/desktop/src/shared/ui/link-preview-list.tsx
+++ b/desktop/src/shared/ui/link-preview-list.tsx
@@ -1,5 +1,6 @@
 import { useState } from "react";
 
+import { useLinkPreviewStyle } from "@/shared/lib/linkPreviewStylePreference";
 import type { ResolvedLinkPreview } from "@/shared/lib/useResolvedLinkPreviews";
 import {
   AlertDialog,
@@ -14,30 +15,40 @@ import {
 import { AttachmentGroup } from "@/shared/ui/attachment";
 import { Button } from "@/shared/ui/button";
 import { LinkPreviewAttachment } from "@/shared/ui/link-preview-attachment";
+import type { LinkPreviewImageLightboxComponent } from "@/shared/ui/rich-link-preview-attachment";
 
 export function LinkPreviewList({
+  ImageLightbox,
   onRemoveForEveryone,
   previews,
 }: {
+  ImageLightbox: LinkPreviewImageLightboxComponent;
   onRemoveForEveryone?: () => Promise<void>;
   previews: ResolvedLinkPreview[];
 }) {
   const [dialogOpen, setDialogOpen] = useState(false);
   const [removed, setRemoved] = useState(false);
+  const style = useLinkPreviewStyle();
   if (removed || previews.length === 0) return null;
 
   const previewNoun = previews.length === 1 ? "preview" : "previews";
+  const removeButtonIndex = style === "compact" ? previews.length - 1 : 0;
   return (
     <>
       <AttachmentGroup
-        className="max-w-full flex-col items-start overflow-visible pb-0"
+        className={
+          style === "compact"
+            ? "max-w-full flex-row flex-wrap items-start overflow-visible pb-0"
+            : "max-w-full flex-col items-start overflow-visible pb-0"
+        }
         data-link-preview-list=""
       >
         {previews.map((preview, index) => (
           <LinkPreviewAttachment
             key={preview.href}
+            ImageLightbox={ImageLightbox}
             onRemove={
-              onRemoveForEveryone && index === 0
+              onRemoveForEveryone && index === removeButtonIndex
                 ? () => setDialogOpen(true)
                 : undefined
             }
diff --git a/desktop/src/shared/ui/markdown.tsx b/desktop/src/shared/ui/markdown.tsx
index 4a2aa802e..1a3718b8c 100644
--- a/desktop/src/shared/ui/markdown.tsx
+++ b/desktop/src/shared/ui/markdown.tsx
@@ -61,6 +61,7 @@ import {
 } from "./markdown/CodeBlock";
 import { FileCard } from "./markdown/FileCard";
 import { InlineEmojiPopover } from "./markdown/InlineEmojiPopover";
+import { createLinkPreviewImageLightbox } from "./markdown/LinkPreviewImageLightbox";
 import { MarkdownInput } from "./markdown/MarkdownInput";
 import {
   MediaContextMenu,
@@ -93,6 +94,7 @@ import {
   IMAGE_LIGHTBOX_WHEEL_ZOOM_SPEED,
   IMAGE_LIGHTBOX_ZOOM_STEP,
   IMAGE_LIGHTBOX_ZOOM_TRANSITION_MS,
+  getImageLightboxFocusableElements,
   imageLightboxBasisBoxForItem,
   imageLightboxBoxFromRect,
   imageLightboxCornerRadiiFromElement,
@@ -145,28 +147,6 @@ type WebKitGestureLikeEvent = Event & {
   scale?: number;
 };
 
-function getImageLightboxFocusableElements(
-  container: HTMLElement,
-): HTMLElement[] {
-  return Array.from(
-    container.querySelectorAll<HTMLElement>(
-      [
-        "a[href]",
-        "button:not(:disabled)",
-        "input:not(:disabled)",
-        "select:not(:disabled)",
-        "textarea:not(:disabled)",
-        "[tabindex]:not([tabindex='-1'])",
-      ].join(","),
-    ),
-  ).filter(
-    (element) =>
-      !element.hasAttribute("disabled") &&
-      element.getAttribute("aria-hidden") !== "true" &&
-      element.getClientRects().length > 0,
-  );
-}
-
 function ImageZoomOverlay({
   alt,
   galleryIndex = 0,
@@ -995,6 +975,9 @@ function ImageZoomOverlay({
   );
 }
 
+const LinkPreviewImageLightbox =
+  createLinkPreviewImageLightbox(ImageZoomOverlay);
+
 /**
  * Inline image embed with click-to-zoom lightbox and right-click download.
  *
@@ -1973,6 +1956,7 @@ function MarkdownInner({
             </AttachmentGroup>
           ) : null}
           <LinkPreviewList
+            ImageLightbox={LinkPreviewImageLightbox}
             key={messageId}
             onRemoveForEveryone={onRemoveLinkPreviewsForEveryone}
             previews={resolvedLinkPreviews}
diff --git a/desktop/src/shared/ui/markdown/LinkPreviewImageLightbox.tsx b/desktop/src/shared/ui/markdown/LinkPreviewImageLightbox.tsx
new file mode 100644
index 000000000..c689dd9ef
--- /dev/null
+++ b/desktop/src/shared/ui/markdown/LinkPreviewImageLightbox.tsx
@@ -0,0 +1,118 @@
+import type { ComponentType } from "react";
+import { useRef, useState } from "react";
+
+import { cn } from "@/shared/lib/cn";
+import type { LinkPreviewImageLightboxProps } from "@/shared/ui/rich-link-preview-attachment";
+
+import {
+  type ImageGalleryItem,
+  type ImageLightboxBox,
+  type ImageLightboxCornerRadii,
+  imageLightboxBoxFromRect,
+  imageLightboxCornerRadiiFromElement,
+  visibleImageGalleryForTrigger,
+} from "./imageLightbox";
+
+type ImageZoomOverlayProps = {
+  alt: string | undefined;
+  galleryIndex?: number;
+  galleryItems?: ImageGalleryItem[];
+  onClose: () => void;
+  onCopy: (src: string | undefined) => void;
+  onDownload: (src: string | undefined) => void;
+  resolvedSrc: string;
+  sourceBox: ImageLightboxBox;
+  sourceCornerRadii: ImageLightboxCornerRadii;
+  sourceScope?: Element | null;
+  src: string | undefined;
+};
+
+const ignoreUnavailableImageAction = () => undefined;
+
+export function createLinkPreviewImageLightbox(
+  ImageZoomOverlay: ComponentType<ImageZoomOverlayProps>,
+): ComponentType<LinkPreviewImageLightboxProps> {
+  return function LinkPreviewImageLightbox({ alt, children, className, src }) {
+    const [lightboxState, setLightboxState] = useState<{
+      galleryIndex: number;
+      galleryItems?: ImageGalleryItem[];
+      sourceBox: ImageLightboxBox;
+      sourceCornerRadii: ImageLightboxCornerRadii;
+      sourceScope: Element | null;
+    } | null>(null);
+    const triggerRef = useRef<HTMLButtonElement | null>(null);
+
+    const openLightbox = () => {
+      const trigger = triggerRef.current;
+      const image = trigger?.querySelector("img");
+      if (!trigger || !image) return;
+
+      const rect = image.getBoundingClientRect();
+      if (rect.width <= 0 || rect.height <= 0) return;
+
+      const sourceBox = imageLightboxBoxFromRect(rect);
+      const sourceCornerRadii = imageLightboxCornerRadiiFromElement(image);
+      const sourceScope = trigger.closest("[data-link-preview-list]");
+      const dim =
+        image.naturalWidth > 0 && image.naturalHeight > 0
+          ? `${image.naturalWidth}x${image.naturalHeight}`
+          : undefined;
+      const gallery = visibleImageGalleryForTrigger(
+        trigger,
+        {
+          alt,
+          dim,
+          resolvedSrc: src,
+          src: undefined,
+          thumbnailBox: sourceBox,
+          thumbnailCornerRadii: sourceCornerRadii,
+        },
+        sourceScope,
+      );
+
+      setLightboxState({
+        galleryIndex: gallery.galleryIndex,
+        galleryItems: gallery.galleryItems,
+        sourceBox,
+        sourceCornerRadii,
+        sourceScope,
+      });
+    };
+
+    return (
+      <>
+        <button
+          aria-label={`Zoom image: ${alt}`}
+          className={cn(
+            "cursor-zoom-in border-0 p-0 text-left focus:outline-hidden focus-visible:ring-2 focus-visible:ring-ring/50",
+            lightboxState && "opacity-0",
+            className,
+          )}
+          data-image-lightbox-alt={alt}
+          data-image-lightbox-resolved-src={src}
+          data-image-lightbox-trigger=""
+          onClick={openLightbox}
+          ref={triggerRef}
+          type="button"
+        >
+          {children}
+        </button>
+        {lightboxState ? (
+          <ImageZoomOverlay
+            alt={alt}
+            galleryIndex={lightboxState.galleryIndex}
+            galleryItems={lightboxState.galleryItems}
+            onClose={() => setLightboxState(null)}
+            onCopy={ignoreUnavailableImageAction}
+            onDownload={ignoreUnavailableImageAction}
+            resolvedSrc={src}
+            sourceBox={lightboxState.sourceBox}
+            sourceCornerRadii={lightboxState.sourceCornerRadii}
+            sourceScope={lightboxState.sourceScope}
+            src={undefined}
+          />
+        ) : null}
+      </>
+    );
+  };
+}
diff --git a/desktop/src/shared/ui/markdown/imageLightbox.ts b/desktop/src/shared/ui/markdown/imageLightbox.ts
index 1c57cb9e5..4c0c01f93 100644
--- a/desktop/src/shared/ui/markdown/imageLightbox.ts
+++ b/desktop/src/shared/ui/markdown/imageLightbox.ts
@@ -316,9 +316,15 @@ function imageGalleryItemFromTrigger(
     return null;
   }
 
+  const image = trigger.querySelector("img");
+  const inferredDim =
+    image && image.naturalWidth > 0 && image.naturalHeight > 0
+      ? `${image.naturalWidth}x${image.naturalHeight}`
+      : undefined;
+
   return {
     alt: trigger.dataset.imageLightboxAlt || undefined,
-    dim: trigger.dataset.imageLightboxDim || undefined,
+    dim: trigger.dataset.imageLightboxDim || inferredDim,
     resolvedSrc,
     src: trigger.dataset.imageLightboxSrc || undefined,
     thumbnailBox: thumbnail?.box,
@@ -403,3 +409,25 @@ export function visibleImageGalleryForTrigger(
     galleryItems: galleryItems.length > 1 ? galleryItems : undefined,
   };
 }
+
+export function getImageLightboxFocusableElements(
+  container: HTMLElement,
+): HTMLElement[] {
+  return Array.from(
+    container.querySelectorAll<HTMLElement>(
+      [
+        "a[href]",
+        "button:not(:disabled)",
+        "input:not(:disabled)",
+        "select:not(:disabled)",
+        "textarea:not(:disabled)",
+        "[tabindex]:not([tabindex='-1'])",
+      ].join(","),
+    ),
+  ).filter(
+    (element) =>
+      !element.hasAttribute("disabled") &&
+      element.getAttribute("aria-hidden") !== "true" &&
+      element.getClientRects().length > 0,
+  );
+}
diff --git a/desktop/src/shared/ui/rich-link-preview-attachment.tsx b/desktop/src/shared/ui/rich-link-preview-attachment.tsx
index f2728cfa9..c906e1d4e 100644
--- a/desktop/src/shared/ui/rich-link-preview-attachment.tsx
+++ b/desktop/src/shared/ui/rich-link-preview-attachment.tsx
@@ -1,10 +1,20 @@
 import { ChevronDown, ChevronUp, X } from "lucide-react";
+import type { ComponentType, ReactNode } from "react";
 import { useState } from "react";
 
 import type { ResolvedLinkPreview } from "@/shared/lib/useResolvedLinkPreviews";
 import { cn } from "@/shared/lib/cn";
 import { Button } from "@/shared/ui/button";
-import { SimpleImageLightbox } from "@/shared/ui/SimpleImageLightbox";
+
+export type LinkPreviewImageLightboxProps = {
+  alt: string;
+  children: ReactNode;
+  className?: string;
+  src: string;
+};
+
+export type LinkPreviewImageLightboxComponent =
+  ComponentType<LinkPreviewImageLightboxProps>;
 
 function LinkPreviewIdentity({ preview }: { preview: ResolvedLinkPreview }) {
   if (preview.faviconDataUrl) {
@@ -44,13 +54,14 @@ function isTweetPreview(preview: ResolvedLinkPreview): boolean {
 function LinkPreviewImage({
   aspectClassName,
   className,
+  ImageLightbox,
   preview,
 }: {
   aspectClassName: string;
   className?: string;
+  ImageLightbox: LinkPreviewImageLightboxComponent;
   preview: ResolvedLinkPreview;
 }) {
-  const [lightboxOpen, setLightboxOpen] = useState(false);
   const imageSrc =
     preview.imageState === "image" ? preview.imageDataUrl : undefined;
   const alt = `Preview from ${preview.imageDomain}`;
@@ -73,32 +84,22 @@ function LinkPreviewImage({
   }
 
   return (
-    <>
-      <button
-        aria-label={`Open ${alt.toLowerCase()} in lightbox`}
-        className={cn(
-          "block cursor-zoom-in overflow-hidden rounded-xl bg-muted",
-          className,
-        )}
+    <ImageLightbox
+      alt={alt}
+      className={cn("block overflow-hidden rounded-xl bg-muted", className)}
+      src={imageSrc}
+    >
+      <div
+        className={cn("w-full", aspectClassName)}
         data-link-preview-thumbnail=""
-        onClick={() => setLightboxOpen(true)}
-        type="button"
       >
-        <div className={cn("w-full", aspectClassName)}>
-          <img
-            alt={alt}
-            className="h-full w-full object-cover"
-            src={imageSrc}
-          />
-        </div>
-      </button>
-      <SimpleImageLightbox
-        alt={alt}
-        onOpenChange={setLightboxOpen}
-        open={lightboxOpen}
-        src={imageSrc}
-      />
-    </>
+        <img
+          alt={alt}
+          className="h-full w-full rounded-xl object-cover"
+          src={imageSrc}
+        />
+      </div>
+    </ImageLightbox>
   );
 }
 
@@ -125,10 +126,12 @@ function LinkPreviewDescription({
 
 function TweetPreview({
   className,
+  ImageLightbox,
   onRemove,
   preview,
 }: {
   className?: string;
+  ImageLightbox: LinkPreviewImageLightboxComponent;
   onRemove?: () => void;
   preview: ResolvedLinkPreview;
 }) {
@@ -171,6 +174,7 @@ function TweetPreview({
         <LinkPreviewImage
           aspectClassName="aspect-video"
           className="mt-2 w-full max-w-75"
+          ImageLightbox={ImageLightbox}
           preview={preview}
         />
       ) : null}
@@ -208,10 +212,12 @@ function TweetPreview({
 
 export function RichLinkPreviewAttachment({
   className,
+  ImageLightbox,
   onRemove,
   preview,
 }: {
   className?: string;
+  ImageLightbox: LinkPreviewImageLightboxComponent;
   onRemove?: () => void;
   preview: ResolvedLinkPreview;
 }) {
@@ -221,6 +227,7 @@ export function RichLinkPreviewAttachment({
     return (
       <TweetPreview
         className={className}
+        ImageLightbox={ImageLightbox}
         onRemove={onRemove}
         preview={preview}
       />
@@ -271,6 +278,7 @@ export function RichLinkPreviewAttachment({
         <LinkPreviewImage
           aspectClassName="aspect-[1.91/1]"
           className="mt-2 w-full max-w-75"
+          ImageLightbox={ImageLightbox}
           preview={preview}
         />
       ) : null}