diff --git a/apps/api/src/index.ts b/apps/api/src/index.ts
index 968e2600..98505306 100644
--- a/apps/api/src/index.ts
+++ b/apps/api/src/index.ts
@@ -10,6 +10,7 @@ import { db, schema } from "./db/index.js";
 import { runMigrations } from "./db/migrate.js";
 import { captureException, initAnalytics, shutdownAnalytics } from "./lib/analytics.js";
 import { startCleanupCron } from "./lib/cleanup.js";
+import { buildCsp } from "./lib/csp.js";
 import { ensureAiDirs, recoverInterruptedInstalls } from "./lib/feature-status.js";
 import { shutdownWorkerPool } from "./lib/worker-pool.js";
 import { requirePermission } from "./permissions.js";
@@ -127,10 +128,7 @@ app.addHook("onSend", async (_request, reply) => {
   reply.header("Permissions-Policy", "camera=(), microphone=(), geolocation=()");
   if (process.env.NODE_ENV === "production") {
     reply.header("Strict-Transport-Security", "max-age=31536000; includeSubDomains");
-    const csp = _request.url.startsWith("/api/docs")
-      ? "default-src 'self'; script-src 'self' 'unsafe-inline'; style-src 'self' 'unsafe-inline'; img-src 'self' blob: data:; connect-src 'self'; font-src 'self' data:; object-src 'none'; base-uri 'self'; form-action 'self'"
-      : "default-src 'self'; script-src 'self'; style-src 'self' 'unsafe-inline'; img-src 'self' blob: data: https://tile.openstreetmap.org; connect-src 'self'; font-src 'self' data:; object-src 'none'; frame-ancestors 'none'; base-uri 'self'; form-action 'self'";
-    reply.header("Content-Security-Policy", csp);
+    reply.header("Content-Security-Policy", buildCsp(_request.url.startsWith("/api/docs")));
   }
 });
 
diff --git a/apps/api/src/lib/csp.ts b/apps/api/src/lib/csp.ts
new file mode 100644
index 00000000..b5bfa269
--- /dev/null
+++ b/apps/api/src/lib/csp.ts
@@ -0,0 +1,17 @@
+const POSTHOG_ORIGINS = ["https://us.i.posthog.com", "https://us-assets.i.posthog.com"];
+const SENTRY_ORIGINS = ["https://*.ingest.us.sentry.io"];
+const SCALAR_FONT_ORIGIN = "https://fonts.scalar.com";
+
+export function buildCsp(isDocs: boolean): string {
+  const connectSrc = ["'self'", ...POSTHOG_ORIGINS, ...SENTRY_ORIGINS].join(" ");
+  const fontSrc = isDocs ? `'self' data: ${SCALAR_FONT_ORIGIN}` : "'self' data:";
+  const scriptSrc = isDocs
+    ? "'self' 'unsafe-inline' https://us-assets.i.posthog.com"
+    : "'self' https://us-assets.i.posthog.com";
+
+  if (isDocs) {
+    return `default-src 'self'; script-src ${scriptSrc}; style-src 'self' 'unsafe-inline'; img-src 'self' blob: data:; connect-src ${connectSrc}; font-src ${fontSrc}; object-src 'none'; base-uri 'self'; form-action 'self'`;
+  }
+
+  return `default-src 'self'; script-src ${scriptSrc}; style-src 'self' 'unsafe-inline'; img-src 'self' blob: data: https://tile.openstreetmap.org; connect-src ${connectSrc}; font-src ${fontSrc}; object-src 'none'; frame-ancestors 'none'; base-uri 'self'; form-action 'self'`;
+}
diff --git a/apps/api/src/routes/branding.ts b/apps/api/src/routes/branding.ts
index ae8e81be..720c9a62 100644
--- a/apps/api/src/routes/branding.ts
+++ b/apps/api/src/routes/branding.ts
@@ -16,7 +16,7 @@ import { db, schema } from "../db/index.js";
 import { ensureSharpCompat } from "../lib/heic-converter.js";
 import { requirePermission } from "../permissions.js";
 
-const BRANDING_DIR = join(process.cwd(), "data", "branding");
+const BRANDING_DIR = join(env.FILES_STORAGE_PATH, "branding");
 const LOGO_PATH = join(BRANDING_DIR, "logo.png");
 const maxLogoSize = env.MAX_LOGO_SIZE_KB * 1024;
 
diff --git a/apps/web/src/components/settings/settings-dialog.tsx b/apps/web/src/components/settings/settings-dialog.tsx
index a70b7fe9..b331826f 100644
--- a/apps/web/src/components/settings/settings-dialog.tsx
+++ b/apps/web/src/components/settings/settings-dialog.tsx
@@ -2292,6 +2292,7 @@ function AuditLogSection() {
 function ToolsSection() {
   const [disabledTools, setDisabledTools] = useState<string[]>([]);
   const [loading, setLoading] = useState(true);
+  const [loadFailed, setLoadFailed] = useState(false);
   const [saving, setSaving] = useState(false);
   const [search, setSearch] = useState("");
   const [showRestartBanner, setShowRestartBanner] = useState(false);
@@ -2302,8 +2303,9 @@ function ToolsSection() {
         setDisabledTools(
           data.settings.disabledTools ? JSON.parse(data.settings.disabledTools) : [],
         );
+        setLoadFailed(false);
       })
-      .catch(() => {})
+      .catch(() => setLoadFailed(true))
       .finally(() => setLoading(false));
   }, []);
 
@@ -2424,11 +2426,17 @@ function ToolsSection() {
         </p>
       )}
 
+      {loadFailed && (
+        <div className="px-4 py-3 rounded-lg border border-red-500/30 bg-red-500/10 text-sm text-red-700 dark:text-red-400">
+          Failed to load tool settings. Saving is disabled to prevent data loss.
+        </div>
+      )}
+
       <div className="flex items-center gap-3 pt-2">
         <button
           type="button"
           onClick={handleSave}
-          disabled={saving}
+          disabled={saving || loadFailed}
           className="flex items-center gap-2 px-4 py-2 rounded-lg bg-primary text-primary-foreground text-sm font-medium hover:bg-primary/90 transition-colors disabled:opacity-50"
         >
           {saving && <Loader2 className="h-3.5 w-3.5 animate-spin" />}
diff --git a/apps/web/src/lib/analytics.ts b/apps/web/src/lib/analytics.ts
index f1fc4147..cd92bab1 100644
--- a/apps/web/src/lib/analytics.ts
+++ b/apps/web/src/lib/analytics.ts
@@ -16,12 +16,10 @@ function scrubString(str: string): string {
 
 export async function initAnalytics(config: AnalyticsConfig): Promise<void> {
   if (initialized || !config.enabled) return;
-  initialized = true;
 
   try {
     const posthogJs = (await import("posthog-js")).default;
     if (!consentGranted) {
-      initialized = false;
       return;
     }
     posthog =
@@ -39,15 +37,15 @@ export async function initAnalytics(config: AnalyticsConfig): Promise<void> {
         ip: false,
         persistence: "localStorage",
       }) ?? null;
-  } catch {
-    // SDK blocked or unavailable
+    initialized = true;
+  } catch (err) {
+    console.warn("[analytics] PostHog init failed:", err);
   }
 
   try {
     if (config.sentryDsn) {
       const Sentry = await import("@sentry/react");
       if (!consentGranted) {
-        initialized = false;
         return;
       }
       Sentry.init({
@@ -86,8 +84,8 @@ export async function initAnalytics(config: AnalyticsConfig): Promise<void> {
         },
       });
     }
-  } catch {
-    // Sentry blocked or unavailable
+  } catch (err) {
+    console.warn("[analytics] Sentry init failed:", err);
   }
 }
 
diff --git a/apps/web/src/stores/features-store.ts b/apps/web/src/stores/features-store.ts
index fb3f0bc9..fe24ecdd 100644
--- a/apps/web/src/stores/features-store.ts
+++ b/apps/web/src/stores/features-store.ts
@@ -11,6 +11,7 @@ interface BundleProgress {
 interface FeaturesState {
   bundles: FeatureBundleState[];
   loaded: boolean;
+  loadError: boolean;
   installing: Record<string, BundleProgress>;
   errors: Record<string, string>;
   queued: string[];
@@ -149,6 +150,7 @@ export const useFeaturesStore = create<FeaturesState>((set, get) => {
   return {
     bundles: [],
     loaded: false,
+    loadError: false,
     installing: {},
     errors: {},
     queued: [],
@@ -156,13 +158,13 @@ export const useFeaturesStore = create<FeaturesState>((set, get) => {
     startTimes: {},
 
     fetch: async () => {
-      if (get().loaded) return;
+      if (get().loaded && !get().loadError) return;
       try {
         const data = await apiGet<{ bundles: FeatureBundleState[] }>("/v1/features");
-        set({ bundles: data.bundles, loaded: true });
+        set({ bundles: data.bundles, loaded: true, loadError: false });
         recoverActiveInstalls();
       } catch {
-        set({ loaded: true });
+        set({ loaded: true, loadError: true });
       }
     },
 
diff --git a/apps/web/src/stores/settings-store.ts b/apps/web/src/stores/settings-store.ts
index 1a1abcd8..51f5619a 100644
--- a/apps/web/src/stores/settings-store.ts
+++ b/apps/web/src/stores/settings-store.ts
@@ -10,6 +10,7 @@ interface SettingsState {
   defaultToolView: "sidebar" | "fullscreen";
   defaultTheme: Theme;
   loaded: boolean;
+  loadError: boolean;
   fetch: () => Promise<void>;
 }
 
@@ -21,9 +22,10 @@ export const useSettingsStore = create<SettingsState>((set, get) => ({
   defaultToolView: "sidebar",
   defaultTheme: "light",
   loaded: false,
+  loadError: false,
 
   fetch: async () => {
-    if (get().loaded) return;
+    if (get().loaded && !get().loadError) return;
     try {
       const data = await apiGet<{
         settings: Record<string, string>;
@@ -39,11 +41,12 @@ export const useSettingsStore = create<SettingsState>((set, get) => ({
         defaultToolView: data.settings.defaultToolView === "fullscreen" ? "fullscreen" : "sidebar",
         defaultTheme,
         loaded: true,
+        loadError: false,
       });
 
       useThemeStore.getState().applyServerDefault(defaultTheme);
     } catch {
-      set({ loaded: true });
+      set({ loaded: true, loadError: true });
     }
   },
 }));
diff --git a/tests/unit/api/csp.test.ts b/tests/unit/api/csp.test.ts
new file mode 100644
index 00000000..9c1a3b90
--- /dev/null
+++ b/tests/unit/api/csp.test.ts
@@ -0,0 +1,67 @@
+import { describe, expect, it } from "vitest";
+import { buildCsp } from "../../../apps/api/src/lib/csp.js";
+
+function parseDirective(csp: string, directive: string): string[] {
+  const match = csp.match(new RegExp(`${directive}\\s+([^;]+)`));
+  return match ? match[1].trim().split(/\s+/) : [];
+}
+
+describe("buildCsp", () => {
+  describe("connect-src allows analytics domains", () => {
+    it.each([true, false])("includes PostHog ingest (isDocs=%s)", (isDocs) => {
+      const sources = parseDirective(buildCsp(isDocs), "connect-src");
+      expect(sources).toContain("https://us.i.posthog.com");
+    });
+
+    it.each([true, false])("includes PostHog assets (isDocs=%s)", (isDocs) => {
+      const sources = parseDirective(buildCsp(isDocs), "connect-src");
+      expect(sources).toContain("https://us-assets.i.posthog.com");
+    });
+
+    it.each([true, false])("includes Sentry ingest (isDocs=%s)", (isDocs) => {
+      const sources = parseDirective(buildCsp(isDocs), "connect-src");
+      expect(sources).toContain("https://*.ingest.us.sentry.io");
+    });
+
+    it.each([true, false])("keeps self (isDocs=%s)", (isDocs) => {
+      expect(parseDirective(buildCsp(isDocs), "connect-src")).toContain("'self'");
+    });
+  });
+
+  describe("script-src allows PostHog config loader", () => {
+    it.each([true, false])("includes PostHog assets origin (isDocs=%s)", (isDocs) => {
+      const sources = parseDirective(buildCsp(isDocs), "script-src");
+      expect(sources).toContain("https://us-assets.i.posthog.com");
+    });
+
+    it("docs pages allow unsafe-inline for Scalar", () => {
+      expect(parseDirective(buildCsp(true), "script-src")).toContain("'unsafe-inline'");
+    });
+
+    it("app pages do not allow unsafe-inline", () => {
+      expect(parseDirective(buildCsp(false), "script-src")).not.toContain("'unsafe-inline'");
+    });
+  });
+
+  describe("font-src allows Scalar docs fonts", () => {
+    it("docs pages include Scalar fonts origin", () => {
+      const sources = parseDirective(buildCsp(true), "font-src");
+      expect(sources).toContain("https://fonts.scalar.com");
+    });
+
+    it("app pages do not include Scalar fonts origin", () => {
+      const sources = parseDirective(buildCsp(false), "font-src");
+      expect(sources).not.toContain("https://fonts.scalar.com");
+    });
+  });
+
+  it("includes frame-ancestors none for app pages but not docs", () => {
+    expect(buildCsp(false)).toContain("frame-ancestors 'none'");
+    expect(buildCsp(true)).not.toContain("frame-ancestors");
+  });
+
+  it("allows OpenStreetMap tiles in img-src for app pages", () => {
+    const sources = parseDirective(buildCsp(false), "img-src");
+    expect(sources).toContain("https://tile.openstreetmap.org");
+  });
+});
diff --git a/tests/unit/web/analytics.test.ts b/tests/unit/web/analytics.test.ts
index 9d5e90e7..6a500f88 100644
--- a/tests/unit/web/analytics.test.ts
+++ b/tests/unit/web/analytics.test.ts
@@ -132,6 +132,28 @@ describe("analytics lib", () => {
       expect(mockInit).toHaveBeenCalledOnce();
     });
 
+    it("retries initialization if first attempt throws", async () => {
+      setAnalyticsConsent(true);
+      mockInit.mockImplementationOnce(() => {
+        throw new Error("init failed");
+      });
+      await initAnalytics(enabledConfig);
+      expect(mockInit).toHaveBeenCalledOnce();
+
+      mockInit.mockClear();
+      mockInit.mockReturnValueOnce({
+        capture: mockCapture,
+        identify: mockIdentify,
+        startSessionRecording: mockStartSessionRecording,
+        opt_in_capturing: mockOptIn,
+        opt_out_capturing: mockOptOut,
+        reset: mockReset,
+        persistence: { disabled: false },
+      });
+      await initAnalytics(enabledConfig);
+      expect(mockInit).toHaveBeenCalledOnce();
+    });
+
     it("bails out if consent is revoked during async import", async () => {
       setAnalyticsConsent(true);
       const initPromise = initAnalytics(enabledConfig);
diff --git a/tests/unit/web/zustand-stores.test.ts b/tests/unit/web/zustand-stores.test.ts
index f79bd059..317b0661 100644
--- a/tests/unit/web/zustand-stores.test.ts
+++ b/tests/unit/web/zustand-stores.test.ts
@@ -1697,6 +1697,7 @@ describe("useSettingsStore", () => {
       defaultToolView: "sidebar",
       defaultTheme: "light",
       loaded: false,
+      loadError: false,
     });
     localStorage.removeItem("snapotter-theme-user-set");
     mockApiGet.mockReset();
@@ -1765,8 +1766,8 @@ describe("useSettingsStore", () => {
     expect(useSettingsStore.getState().defaultTheme).toBe("light");
   });
 
-  it("fetch skips when already loaded", async () => {
-    useSettingsStore.setState({ loaded: true });
+  it("fetch skips when already loaded without error", async () => {
+    useSettingsStore.setState({ loaded: true, loadError: false });
     await useSettingsStore.getState().fetch();
     expect(mockApiGet).not.toHaveBeenCalled();
   });
@@ -1797,14 +1798,29 @@ describe("useSettingsStore", () => {
     expect(useSettingsStore.getState().defaultToolView).toBe("sidebar");
   });
 
-  it("fetch sets loaded=true on error", async () => {
+  it("fetch sets loaded=true and loadError=true on error", async () => {
     mockApiGet.mockRejectedValueOnce(new Error("Network error"));
 
     await useSettingsStore.getState().fetch();
 
     expect(useSettingsStore.getState().loaded).toBe(true);
+    expect(useSettingsStore.getState().loadError).toBe(true);
     expect(useSettingsStore.getState().disabledTools).toEqual([]);
   });
+
+  it("fetch retries when loadError is true", async () => {
+    mockApiGet.mockRejectedValueOnce(new Error("Network error"));
+    await useSettingsStore.getState().fetch();
+    expect(useSettingsStore.getState().loadError).toBe(true);
+
+    mockApiGet.mockResolvedValueOnce({
+      settings: { disabledTools: JSON.stringify(["resize"]) },
+    });
+    await useSettingsStore.getState().fetch();
+
+    expect(useSettingsStore.getState().loadError).toBe(false);
+    expect(useSettingsStore.getState().disabledTools).toEqual(["resize"]);
+  });
 });
 
 // ==========================================================================
@@ -1835,6 +1851,7 @@ describe("useFeaturesStore", () => {
     useFeaturesStore.setState({
       bundles: [],
       loaded: false,
+      loadError: false,
       installing: {},
       errors: {},
       queued: [],
@@ -1877,19 +1894,45 @@ describe("useFeaturesStore", () => {
     expect(s.loaded).toBe(true);
   });
 
-  it("fetch skips when already loaded", async () => {
-    useFeaturesStore.setState({ loaded: true });
+  it("fetch skips when already loaded without error", async () => {
+    useFeaturesStore.setState({ loaded: true, loadError: false });
     await useFeaturesStore.getState().fetch();
     expect(mockApiGet).not.toHaveBeenCalled();
   });
 
-  it("fetch sets loaded=true on error", async () => {
+  it("fetch sets loaded=true and loadError=true on error", async () => {
     mockApiGet.mockRejectedValueOnce(new Error("Network error"));
     await useFeaturesStore.getState().fetch();
     expect(useFeaturesStore.getState().loaded).toBe(true);
+    expect(useFeaturesStore.getState().loadError).toBe(true);
     expect(useFeaturesStore.getState().bundles).toEqual([]);
   });
 
+  it("fetch retries when loadError is true", async () => {
+    mockApiGet.mockRejectedValueOnce(new Error("Network error"));
+    await useFeaturesStore.getState().fetch();
+    expect(useFeaturesStore.getState().loadError).toBe(true);
+
+    const bundles = [
+      {
+        id: "ai-rembg",
+        name: "AI Background Remover",
+        description: "Remove backgrounds",
+        status: "installed" as const,
+        installedVersion: "1.0.0",
+        estimatedSize: "500MB",
+        enablesTools: ["remove-bg"],
+        progress: null,
+        error: null,
+      },
+    ];
+    mockApiGet.mockResolvedValueOnce({ bundles });
+    await useFeaturesStore.getState().fetch();
+
+    expect(useFeaturesStore.getState().loadError).toBe(false);
+    expect(useFeaturesStore.getState().bundles).toEqual(bundles);
+  });
+
   it("isToolInstalled returns true for tools whose bundle is installed", () => {
     useFeaturesStore.setState({
       bundles: [