diff --git a/.taskfiles/desktop.yml b/.taskfiles/desktop.yml
index c80196305b..8ae6ddfa6e 100644
--- a/.taskfiles/desktop.yml
+++ b/.taskfiles/desktop.yml
@@ -78,6 +78,16 @@ tasks:
     cmds:
       - npx tauri build --bundles nsis --config '{"bundle":{"createUpdaterArtifacts":false}}'
 
+  build:msi:
+    desc: "Build Tauri desktop MSI installer with bundled JRE (Windows)"
+    deps: [prepare]
+    dir: editor
+    platforms: [windows]
+    cmds:
+      # prepare -> jlink (real bundled JRE) + jar + frontend + provisioner.
+      # No updater artifacts, so no signing key is required for a local MSI.
+      - npx tauri build --bundles msi --config '{"bundle":{"createUpdaterArtifacts":false}}'
+
   build:dev:linux:
     desc: "Build Tauri desktop AppImage (Linux)"
     deps: [prepare]
@@ -194,7 +204,12 @@ tasks:
       # `desktop:build` run `jlink:clean` first to force a fresh build.
       - cmd: chmod -R u+w runtime/jre
         platforms: [linux, darwin]
-      - cmd: powershell -NoProfile -Command "Get-ChildItem -Recurse runtime/jre | ForEach-Object { $_.IsReadOnly = $false }"
+      # Single-quote the PowerShell so go-task's POSIX shell passes $_ and $false
+      # through literally. With double quotes it expands $_ to the task path and
+      # $false to empty, so read-only never clears and the next incremental build
+      # dies with "Permission denied (os error 13)" staging the JRE. -File keeps
+      # it to FileInfo (only files carry a settable IsReadOnly).
+      - cmd: powershell -NoProfile -Command 'Get-ChildItem -Recurse -Force -File runtime/jre | ForEach-Object { $_.IsReadOnly = $false }'
         platforms: [windows]
     status:
       - test -f runtime/jre/release
diff --git a/frontend/editor/public/locales/en-US/translation.toml b/frontend/editor/public/locales/en-US/translation.toml
index c182ce2b89..abb0f7ad95 100644
--- a/frontend/editor/public/locales/en-US/translation.toml
+++ b/frontend/editor/public/locales/en-US/translation.toml
@@ -3655,6 +3655,7 @@ shareSelected = "Share Files"
 sharing = "Sharing"
 showAll = "Show All"
 showHistory = "Show History"
+showInFolder = "Show in folder"
 sortByDate = "Sort by Date"
 sortByName = "Sort by Name"
 sortBySize = "Sort by Size"
diff --git a/frontend/editor/src-tauri/src/commands/files.rs b/frontend/editor/src-tauri/src/commands/files.rs
index 1e3c9b61cb..71ae4abe33 100644
--- a/frontend/editor/src-tauri/src/commands/files.rs
+++ b/frontend/editor/src-tauri/src/commands/files.rs
@@ -1,5 +1,6 @@
 use crate::utils::add_log;
 use std::sync::Mutex;
+use tauri_plugin_opener::OpenerExt;
 
 // Store the opened file paths globally (supports multiple files)
 static OPENED_FILES: Mutex<Vec<String>> = Mutex::new(Vec::new());
@@ -42,3 +43,41 @@ pub async fn pop_opened_files() -> Result<Vec<String>, String> {
     add_log(format!("📂 Returning and clearing {} opened file(s)", all_files.len()));
     Ok(all_files)
 }
+
+// Report whether a path still exists on disk (used to prune stale recent files).
+#[tauri::command]
+pub fn path_exists(path: String) -> bool {
+    std::path::Path::new(&path).exists()
+}
+
+// Reveal a file in the OS file manager (Explorer/Finder), highlighting it.
+#[tauri::command]
+pub async fn reveal_in_file_manager(app: tauri::AppHandle, path: String) -> Result<(), String> {
+    app.opener()
+        .reveal_item_in_dir(&path)
+        .map_err(|e| e.to_string())
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use std::io::Write;
+
+    #[test]
+    fn path_exists_tracks_real_disk_state() {
+        let file = std::env::temp_dir()
+            .join(format!("stirling_path_exists_{}.tmp", std::process::id()));
+        let path = file.to_string_lossy().to_string();
+
+        // Absent before creation.
+        assert!(!path_exists(path.clone()));
+
+        // Present once written.
+        writeln!(std::fs::File::create(&file).unwrap(), "x").unwrap();
+        assert!(path_exists(path.clone()));
+
+        // Gone again after deletion (the case that prunes a recent).
+        std::fs::remove_file(&file).unwrap();
+        assert!(!path_exists(path));
+    }
+}
diff --git a/frontend/editor/src-tauri/src/commands/mod.rs b/frontend/editor/src-tauri/src/commands/mod.rs
index 1637c926c7..6a8b5b5cf7 100644
--- a/frontend/editor/src-tauri/src/commands/mod.rs
+++ b/frontend/editor/src-tauri/src/commands/mod.rs
@@ -10,7 +10,10 @@ pub mod updater;
 pub mod window;
 
 pub use backend::{cleanup_backend, get_backend_port, start_backend};
-pub use files::{add_opened_file, clear_opened_files, get_opened_files, pop_opened_files};
+pub use files::{
+    add_opened_file, clear_opened_files, get_opened_files, path_exists, pop_opened_files,
+    reveal_in_file_manager,
+};
 pub use window::{
     forward_files_to_window,
     open_files_in_new_window,
diff --git a/frontend/editor/src-tauri/src/lib.rs b/frontend/editor/src-tauri/src/lib.rs
index 8855604624..768f791b86 100644
--- a/frontend/editor/src-tauri/src/lib.rs
+++ b/frontend/editor/src-tauri/src/lib.rs
@@ -19,8 +19,10 @@ use commands::{
     get_opened_files,
     open_files_in_new_window,
     open_in_new_window,
+    path_exists,
     pop_opened_files,
     pop_window_file_ids,
+    reveal_in_file_manager,
     get_refresh_token,
     get_user_info,
     is_first_launch,
@@ -167,6 +169,8 @@ pub fn run() {
       get_opened_files,
       pop_opened_files,
       clear_opened_files,
+      path_exists,
+      reveal_in_file_manager,
       open_in_new_window,
       open_files_in_new_window,
       pop_window_file_ids,
diff --git a/frontend/editor/src/core/components/fileManager/FileListItem.tsx b/frontend/editor/src/core/components/fileManager/FileListItem.tsx
index ba1fe52bc9..6ab6b9415a 100644
--- a/frontend/editor/src/core/components/fileManager/FileListItem.tsx
+++ b/frontend/editor/src/core/components/fileManager/FileListItem.tsx
@@ -19,6 +19,7 @@ import CloseIcon from "@mui/icons-material/Close";
 import CloudUploadIcon from "@mui/icons-material/CloudUpload";
 import CloudDoneIcon from "@mui/icons-material/CloudDone";
 import LinkIcon from "@mui/icons-material/Link";
+import FolderOpenIcon from "@mui/icons-material/FolderOpen";
 import { useTranslation } from "react-i18next";
 import { getFileSize, getFileDate } from "@app/utils/fileUtils";
 import { FileId, StirlingFileStub } from "@app/types/fileContext";
@@ -35,6 +36,10 @@ import ShareManagementModal from "@app/components/shared/ShareManagementModal";
 import apiClient from "@app/services/apiClient";
 import { absoluteWithBasePath } from "@app/constants/app";
 import { alert } from "@app/components/toast";
+import {
+  desktopFileLinkingSupported,
+  revealPathInFileManager,
+} from "@app/services/desktopFileLink";
 
 interface FileListItemProps {
   file: StirlingFileStub;
@@ -368,6 +373,18 @@ const FileListItem: React.FC<FileListItemProps> = ({
                 </Menu.Item>
               )}
 
+              {desktopFileLinkingSupported && file.localFilePath && (
+                <Menu.Item
+                  leftSection={<FolderOpenIcon style={{ fontSize: 16 }} />}
+                  onClick={(e) => {
+                    e.stopPropagation();
+                    void revealPathInFileManager(file.localFilePath!);
+                  }}
+                >
+                  {t("fileManager.showInFolder", "Show in folder")}
+                </Menu.Item>
+              )}
+
               {canUpload && (
                 <Menu.Item
                   leftSection={<CloudUploadIcon style={{ fontSize: 16 }} />}
diff --git a/frontend/editor/src/core/hooks/useFileManager.ts b/frontend/editor/src/core/hooks/useFileManager.ts
index 442027364e..2ae2ec2f15 100644
--- a/frontend/editor/src/core/hooks/useFileManager.ts
+++ b/frontend/editor/src/core/hooks/useFileManager.ts
@@ -5,6 +5,12 @@ import { StirlingFileStub, StirlingFile } from "@app/types/fileContext";
 import { FileId } from "@app/types/fileContext";
 import apiClient from "@app/services/apiClient";
 import { useAppConfig } from "@app/contexts/AppConfigContext";
+import {
+  pruneMissingRecentFiles,
+  reconcileServerBackedRecents,
+  hasLocalRecord,
+} from "@app/services/pruneMissingRecentFiles";
+import { desktopFileLinkingSupported } from "@app/services/desktopFileLink";
 
 interface StoredFileResponse {
   id: number;
@@ -105,7 +111,10 @@ export const useFileManager = () => {
       }
 
       // Load only leaf files metadata (processed files that haven't been used as input for other tools)
-      const stirlingFileStubs = await fileStorage.getLeafStirlingFileStubs();
+      // On desktop, drop entries whose linked file no longer exists on disk.
+      const stirlingFileStubs = await pruneMissingRecentFiles(
+        await fileStorage.getLeafStirlingFileStubs(),
+      );
       const remoteIdSet = new Set(
         stirlingFileStubs
           .map((stub) => stub.remoteStorageId)
@@ -133,7 +142,21 @@ export const useFileManager = () => {
             }
           });
 
-          const updatedLocalStubs = stirlingFileStubs.map((stub) => {
+          // Desktop: a server-uploaded recent whose local disk original was
+          // deleted drops its local copy, becoming a pure server file — it
+          // leaves recents but stays under My Files, downloadable. Gated on the
+          // server confirming it holds the file, so the last copy is never lost.
+          let localStubs = stirlingFileStubs;
+          const demotedIds = await reconcileServerBackedRecents(
+            stirlingFileStubs,
+            (id) => serverMap.has(id),
+          );
+          if (demotedIds.length > 0) {
+            const removedSet = new Set(demotedIds);
+            localStubs = stirlingFileStubs.filter((s) => !removedSet.has(s.id));
+          }
+
+          const updatedLocalStubs = localStubs.map((stub) => {
             if (!stub.remoteStorageId) {
               return stub;
             }
@@ -351,8 +374,15 @@ export const useFileManager = () => {
         }
       }
 
+      // Desktop recents show only files with a local IndexedDB record; files
+      // that live ONLY on the server (ephemeral server-/shared- stubs, no IDB
+      // row) belong in the My Files view, not here.
+      const recentStubs = desktopFileLinkingSupported
+        ? combinedStubs.filter(hasLocalRecord)
+        : combinedStubs;
+
       // For now, only regular files - drafts will be handled separately in the future
-      const sortedFiles = combinedStubs.sort(
+      const sortedFiles = recentStubs.sort(
         (a, b) => (b.lastModified || 0) - (a.lastModified || 0),
       );
 
diff --git a/frontend/editor/src/core/services/desktopFileLink.ts b/frontend/editor/src/core/services/desktopFileLink.ts
new file mode 100644
index 0000000000..5b95f165c6
--- /dev/null
+++ b/frontend/editor/src/core/services/desktopFileLink.ts
@@ -0,0 +1,14 @@
+// Seam for linking recent files to their real file on disk (desktop only).
+// Non-desktop builds resolve to this no-op default via the @app alias order,
+// so web/SaaS have no disk-linked recents to prune or reveal.
+
+// False on web: the recent-file pruner and "Show in folder" action are skipped.
+export const desktopFileLinkingSupported = false;
+
+// Assume present so the pruner never drops a recent file off the desktop app.
+export async function pathExistsOnDisk(_path: string): Promise<boolean> {
+  return true;
+}
+
+// No OS file manager to reveal into outside the desktop app.
+export async function revealPathInFileManager(_path: string): Promise<void> {}
diff --git a/frontend/editor/src/core/services/fileStorage.ts b/frontend/editor/src/core/services/fileStorage.ts
index 4cdecca9f1..2d872229f5 100644
--- a/frontend/editor/src/core/services/fileStorage.ts
+++ b/frontend/editor/src/core/services/fileStorage.ts
@@ -29,6 +29,7 @@ export interface StoredStirlingFileRecord extends BaseFileMetadata {
   thumbnail?: string;
   thumbnailStoredAt?: number; // Epoch ms - sliding 30-day TTL
   url?: string; // For compatibility with existing components
+  localFilePath?: string; // Original disk path (desktop) - persisted so recents stay disk-linked across reloads
   // Cached classification labels — mirrors the stub field so the sidebar can
   // group by label without re-reading PDF bytes, and it survives versioning.
   // See StirlingFileStub.classificationLabels.
@@ -132,6 +133,7 @@ class FileStorageService {
       data: arrayBuffer,
       thumbnail: stub.thumbnailUrl,
       thumbnailStoredAt: stub.thumbnailUrl ? Date.now() : undefined,
+      localFilePath: stub.localFilePath,
       isLeaf: stub.isLeaf ?? true,
       remoteStorageId: stub.remoteStorageId,
       remoteStorageUpdatedAt: stub.remoteStorageUpdatedAt,
@@ -262,6 +264,7 @@ class FileStorageService {
           lastModified: record.lastModified,
           quickKey: record.quickKey,
           thumbnailUrl: fresh ? record.thumbnail : undefined,
+          localFilePath: record.localFilePath,
           isLeaf: record.isLeaf,
           remoteStorageId: record.remoteStorageId,
           remoteStorageUpdatedAt: record.remoteStorageUpdatedAt,
@@ -322,6 +325,7 @@ class FileStorageService {
               lastModified: record.lastModified,
               quickKey: record.quickKey,
               thumbnailUrl: fresh ? record.thumbnail : undefined,
+              localFilePath: record.localFilePath,
               isLeaf: record.isLeaf,
               remoteStorageId: record.remoteStorageId,
               remoteStorageUpdatedAt: record.remoteStorageUpdatedAt,
@@ -414,6 +418,7 @@ class FileStorageService {
               lastModified: record.lastModified,
               quickKey: record.quickKey,
               thumbnailUrl: fresh ? record.thumbnail : undefined,
+              localFilePath: record.localFilePath,
               isLeaf: record.isLeaf,
               remoteStorageId: record.remoteStorageId,
               remoteStorageUpdatedAt: record.remoteStorageUpdatedAt,
diff --git a/frontend/editor/src/core/services/pruneMissingRecentFiles.test.ts b/frontend/editor/src/core/services/pruneMissingRecentFiles.test.ts
new file mode 100644
index 0000000000..544ac3dc83
--- /dev/null
+++ b/frontend/editor/src/core/services/pruneMissingRecentFiles.test.ts
@@ -0,0 +1,211 @@
+import { describe, expect, test, vi, beforeEach } from "vitest";
+import type { StirlingFileStub } from "@app/types/fileContext";
+import type { FileId } from "@app/types/file";
+
+// Controllable seam + storage doubles.
+const desktopFileLink = vi.hoisted(() => ({
+  desktopFileLinkingSupported: true,
+  pathExistsOnDisk: vi.fn<(path: string) => Promise<boolean>>(),
+}));
+const deleteMultipleStirlingFiles = vi.hoisted(() =>
+  vi.fn<(ids: FileId[]) => Promise<void>>(),
+);
+const updateFileMetadata = vi.hoisted(() =>
+  vi.fn<(id: FileId, updates: object) => Promise<boolean>>(),
+);
+
+vi.mock("@app/services/desktopFileLink", () => desktopFileLink);
+vi.mock("@app/services/fileStorage", () => ({
+  fileStorage: { deleteMultipleStirlingFiles, updateFileMetadata },
+}));
+
+import {
+  pruneMissingRecentFiles,
+  reconcileServerBackedRecents,
+  hasLocalRecord,
+} from "@app/services/pruneMissingRecentFiles";
+
+const stub = (overrides: Partial<StirlingFileStub> = {}): StirlingFileStub => ({
+  id: "file-1" as FileId,
+  name: "report.pdf",
+  type: "application/pdf",
+  size: 1024,
+  lastModified: 0,
+  isLeaf: true,
+  originalFileId: "file-1",
+  versionNumber: 1,
+  ...overrides,
+});
+
+beforeEach(() => {
+  desktopFileLink.desktopFileLinkingSupported = true;
+  desktopFileLink.pathExistsOnDisk.mockReset().mockResolvedValue(true);
+  deleteMultipleStirlingFiles.mockReset().mockResolvedValue(undefined);
+  updateFileMetadata.mockReset().mockResolvedValue(true);
+});
+
+describe("pruneMissingRecentFiles (local-only files)", () => {
+  test("deletes a pristine local-only file whose disk file is gone", async () => {
+    const gone = stub({ id: "gone" as FileId, localFilePath: "/tmp/gone.pdf" });
+    const kept = stub({ id: "kept" as FileId, localFilePath: "/tmp/kept.pdf" });
+    desktopFileLink.pathExistsOnDisk.mockImplementation(
+      async (p) => p === "/tmp/kept.pdf",
+    );
+
+    const result = await pruneMissingRecentFiles([gone, kept]);
+
+    expect(result.map((s) => s.id)).toEqual(["kept"]);
+    expect(deleteMultipleStirlingFiles).toHaveBeenCalledWith(["gone"]);
+    expect(updateFileMetadata).not.toHaveBeenCalled();
+  });
+
+  test("keeps in-app-edited local files but detaches the dead link", async () => {
+    const dirty = stub({
+      id: "dirty" as FileId,
+      localFilePath: "/tmp/dirty.pdf",
+      isDirty: true,
+    });
+    const edited = stub({
+      id: "edited" as FileId,
+      localFilePath: "/tmp/edited.pdf",
+      versionNumber: 2,
+      toolHistory: [{ toolId: "compress" as never, timestamp: 1 }],
+    });
+    desktopFileLink.pathExistsOnDisk.mockResolvedValue(false);
+
+    const result = await pruneMissingRecentFiles([dirty, edited]);
+
+    expect(result.map((s) => s.id).sort()).toEqual(["dirty", "edited"]);
+    expect(result.every((s) => s.localFilePath === undefined)).toBe(true);
+    expect(deleteMultipleStirlingFiles).not.toHaveBeenCalled();
+    expect(updateFileMetadata).toHaveBeenCalledTimes(2);
+  });
+
+  test("leaves server-backed files untouched (handled after the server fetch)", async () => {
+    const remote = stub({
+      id: "remote" as FileId,
+      localFilePath: "/tmp/remote.pdf",
+      remoteStorageId: 7,
+    });
+    desktopFileLink.pathExistsOnDisk.mockResolvedValue(false);
+
+    const result = await pruneMissingRecentFiles([remote]);
+
+    expect(result).toEqual([remote]);
+    expect(desktopFileLink.pathExistsOnDisk).not.toHaveBeenCalled();
+    expect(deleteMultipleStirlingFiles).not.toHaveBeenCalled();
+    expect(updateFileMetadata).not.toHaveBeenCalled();
+  });
+
+  test("ignores files with no disk link (e.g. web/browser uploads)", async () => {
+    const memoryOnly = stub({ id: "mem" as FileId });
+    desktopFileLink.pathExistsOnDisk.mockResolvedValue(false);
+
+    const result = await pruneMissingRecentFiles([memoryOnly]);
+
+    expect(result).toEqual([memoryOnly]);
+    expect(desktopFileLink.pathExistsOnDisk).not.toHaveBeenCalled();
+  });
+
+  test("is a no-op when desktop file linking is unsupported (web)", async () => {
+    desktopFileLink.desktopFileLinkingSupported = false;
+    const gone = stub({ id: "gone" as FileId, localFilePath: "/tmp/gone.pdf" });
+
+    const result = await pruneMissingRecentFiles([gone]);
+
+    expect(result).toEqual([gone]);
+    expect(desktopFileLink.pathExistsOnDisk).not.toHaveBeenCalled();
+  });
+});
+
+describe("hasLocalRecord (desktop recents = local/IndexedDB only)", () => {
+  test("keeps files with a real local IndexedDB id", () => {
+    expect(hasLocalRecord(stub({ id: "uuid-abc" as FileId }))).toBe(true);
+    // A locally-stored file that is ALSO uploaded still has a local record.
+    expect(
+      hasLocalRecord(stub({ id: "uuid-abc" as FileId, remoteStorageId: 5 })),
+    ).toBe(true);
+  });
+
+  test("excludes ephemeral server-only and shared-only stubs", () => {
+    expect(hasLocalRecord(stub({ id: "server-42" as FileId }))).toBe(false);
+    expect(hasLocalRecord(stub({ id: "shared-tok" as FileId }))).toBe(false);
+  });
+});
+
+describe("reconcileServerBackedRecents (server-uploaded files)", () => {
+  const serverHas = (ids: number[]) => (id: number) => ids.includes(id);
+
+  test("demotes a server-confirmed file whose disk original is gone", async () => {
+    const s = stub({
+      id: "s1" as FileId,
+      localFilePath: "/tmp/s1.pdf",
+      remoteStorageId: 42,
+    });
+    desktopFileLink.pathExistsOnDisk.mockResolvedValue(false);
+
+    const removed = await reconcileServerBackedRecents([s], serverHas([42]));
+
+    expect(removed).toEqual(["s1"]);
+    // The local copy is removed; the file lives on as a pure server file.
+    expect(deleteMultipleStirlingFiles).toHaveBeenCalledWith(["s1"]);
+  });
+
+  test("does NOT demote when the server can't confirm the file (avoids data loss)", async () => {
+    const s = stub({
+      id: "s1" as FileId,
+      localFilePath: "/tmp/s1.pdf",
+      remoteStorageId: 42,
+    });
+    desktopFileLink.pathExistsOnDisk.mockResolvedValue(false);
+
+    const removed = await reconcileServerBackedRecents([s], serverHas([]));
+
+    expect(removed).toEqual([]);
+    expect(desktopFileLink.pathExistsOnDisk).not.toHaveBeenCalled();
+    expect(deleteMultipleStirlingFiles).not.toHaveBeenCalled();
+  });
+
+  test("does NOT demote a file with unsaved local edits", async () => {
+    const s = stub({
+      id: "s1" as FileId,
+      localFilePath: "/tmp/s1.pdf",
+      remoteStorageId: 42,
+      isDirty: true,
+    });
+    desktopFileLink.pathExistsOnDisk.mockResolvedValue(false);
+
+    const removed = await reconcileServerBackedRecents([s], serverHas([42]));
+
+    expect(removed).toEqual([]);
+    expect(deleteMultipleStirlingFiles).not.toHaveBeenCalled();
+  });
+
+  test("does NOT demote when the disk file still exists", async () => {
+    const s = stub({
+      id: "s1" as FileId,
+      localFilePath: "/tmp/s1.pdf",
+      remoteStorageId: 42,
+    });
+    desktopFileLink.pathExistsOnDisk.mockResolvedValue(true);
+
+    const removed = await reconcileServerBackedRecents([s], serverHas([42]));
+
+    expect(removed).toEqual([]);
+    expect(deleteMultipleStirlingFiles).not.toHaveBeenCalled();
+  });
+
+  test("is a no-op off desktop", async () => {
+    desktopFileLink.desktopFileLinkingSupported = false;
+    const s = stub({
+      id: "s1" as FileId,
+      localFilePath: "/tmp/s1.pdf",
+      remoteStorageId: 42,
+    });
+
+    const removed = await reconcileServerBackedRecents([s], serverHas([42]));
+
+    expect(removed).toEqual([]);
+    expect(deleteMultipleStirlingFiles).not.toHaveBeenCalled();
+  });
+});
diff --git a/frontend/editor/src/core/services/pruneMissingRecentFiles.ts b/frontend/editor/src/core/services/pruneMissingRecentFiles.ts
new file mode 100644
index 0000000000..554fc063ea
--- /dev/null
+++ b/frontend/editor/src/core/services/pruneMissingRecentFiles.ts
@@ -0,0 +1,138 @@
+import { StirlingFileStub, FileId } from "@app/types/fileContext";
+import { fileStorage } from "@app/services/fileStorage";
+import {
+  desktopFileLinkingSupported,
+  pathExistsOnDisk,
+} from "@app/services/desktopFileLink";
+
+/**
+ * True for a recents entry backed by a real local IndexedDB record, false for
+ * the ephemeral `server-`/`shared-` stubs synthesised from server storage (which
+ * have no IDB row). Desktop recents show only files with a local record; the
+ * server-only ones belong in the My Files view.
+ */
+export function hasLocalRecord(stub: StirlingFileStub): boolean {
+  return !stub.id.startsWith("server-") && !stub.id.startsWith("shared-");
+}
+
+/**
+ * A local-only recent is a pristine passthrough of its disk file — identical
+ * bytes on disk and in IndexedDB — only if it's a v1 with no in-app edits. When
+ * its disk file disappears there's nothing unique to keep, so it's deleted.
+ * Otherwise (unsaved edits, or a later/tool version) the IndexedDB copy may be
+ * the only one left, so it's KEPT with just the dead disk link detached.
+ */
+function isPristineLocalPassthrough(stub: StirlingFileStub): boolean {
+  return (
+    !stub.isDirty &&
+    (stub.versionNumber ?? 1) === 1 &&
+    (stub.toolHistory?.length ?? 0) === 0
+  );
+}
+
+/**
+ * Reconcile LOCAL-ONLY desktop recents against the disk files they link to.
+ * Server-backed recents are intentionally left untouched here — they're handled
+ * after the server fetch by {@link reconcileServerBackedRecents}, which can
+ * confirm the file still exists remotely before dropping the local copy.
+ *
+ * For each local-only stub whose `localFilePath` no longer exists on disk:
+ *  - pristine passthrough → removed from recents + IndexedDB.
+ *  - edited / dirty       → KEPT, dead `localFilePath` cleared (no broken "Show
+ *    in folder"; Ctrl+S falls back to Save As).
+ * No-op off the desktop app.
+ */
+export async function pruneMissingRecentFiles(
+  stubs: StirlingFileStub[],
+): Promise<StirlingFileStub[]> {
+  if (!desktopFileLinkingSupported) return stubs;
+
+  const linked = stubs.filter(
+    (stub) => stub.localFilePath && !stub.remoteStorageId,
+  );
+  if (linked.length === 0) return stubs;
+
+  const present = await Promise.all(
+    linked.map((stub) => pathExistsOnDisk(stub.localFilePath!)),
+  );
+
+  const toDelete: FileId[] = [];
+  const toDetach: FileId[] = [];
+  linked.forEach((stub, i) => {
+    if (present[i]) return;
+    if (isPristineLocalPassthrough(stub)) toDelete.push(stub.id);
+    else toDetach.push(stub.id);
+  });
+
+  if (toDelete.length === 0 && toDetach.length === 0) return stubs;
+
+  if (toDelete.length > 0) {
+    try {
+      await fileStorage.deleteMultipleStirlingFiles(toDelete);
+    } catch (error) {
+      console.error("[pruneMissingRecentFiles] delete failed:", error);
+    }
+  }
+  if (toDetach.length > 0) {
+    await Promise.all(
+      toDetach.map((id) =>
+        fileStorage
+          .updateFileMetadata(id, { localFilePath: undefined })
+          .catch((error) =>
+            console.error("[pruneMissingRecentFiles] detach failed:", error),
+          ),
+      ),
+    );
+  }
+
+  const deleteSet = new Set<FileId>(toDelete);
+  const detachSet = new Set<FileId>(toDetach);
+  return stubs
+    .filter((stub) => !deleteSet.has(stub.id))
+    .map((stub) =>
+      detachSet.has(stub.id) ? { ...stub, localFilePath: undefined } : stub,
+    );
+}
+
+/**
+ * When a server-uploaded recent's local disk original has been deleted, drop its
+ * LOCAL copy so the file becomes a pure server file: it leaves the (local)
+ * recents but remains under My Files and stays downloadable from the server.
+ * Only files the server CONFIRMS it still holds (via `serverHasFile`) and with
+ * no unsaved local edits are demoted, so the last copy is never lost.
+ *
+ * Returns the deleted local ids so the caller can drop them from the list this
+ * pass. No-op off the desktop app.
+ */
+export async function reconcileServerBackedRecents(
+  stubs: StirlingFileStub[],
+  serverHasFile: (remoteStorageId: number) => boolean,
+): Promise<FileId[]> {
+  if (!desktopFileLinkingSupported) return [];
+
+  const candidates = stubs.filter(
+    (stub) =>
+      typeof stub.remoteStorageId === "number" &&
+      serverHasFile(stub.remoteStorageId) &&
+      stub.localFilePath &&
+      !stub.isDirty,
+  );
+  if (candidates.length === 0) return [];
+
+  const present = await Promise.all(
+    candidates.map((stub) => pathExistsOnDisk(stub.localFilePath!)),
+  );
+  const gone = candidates.filter((_, i) => !present[i]);
+  if (gone.length === 0) return [];
+
+  const removedIds = gone.map((stub) => stub.id);
+  try {
+    await fileStorage.deleteMultipleStirlingFiles(removedIds);
+  } catch (error) {
+    // If we couldn't remove the local copy, don't drop it from the list either.
+    console.error("[reconcileServerBackedRecents] delete failed:", error);
+    return [];
+  }
+
+  return removedIds;
+}
diff --git a/frontend/editor/src/desktop/hooks/useAppInitialization.ts b/frontend/editor/src/desktop/hooks/useAppInitialization.ts
index 176442cb06..4eae0b945f 100644
--- a/frontend/editor/src/desktop/hooks/useAppInitialization.ts
+++ b/frontend/editor/src/desktop/hooks/useAppInitialization.ts
@@ -1,6 +1,7 @@
 import { useEffect, useState } from "react";
 import { useOpenedFile } from "@app/hooks/useOpenedFile";
 import { fileOpenService } from "@app/services/fileOpenService";
+import { fileStorage } from "@app/services/fileStorage";
 import { useFileManagement } from "@app/contexts/file/fileHooks";
 import { createQuickKey } from "@app/types/fileContext";
 
@@ -80,12 +81,18 @@ export function useAppInitialization(): void {
           );
 
           const addedFiles = await addFiles(filesArray, { selectFiles: true });
-          addedFiles.forEach((file) => {
-            const localFilePath = quickKeyToPath.get(file.quickKey);
-            if (localFilePath) {
+          await Promise.all(
+            addedFiles.map(async (file) => {
+              const localFilePath = quickKeyToPath.get(file.quickKey);
+              if (!localFilePath) return;
               updateStirlingFileStub(file.fileId, { localFilePath });
-            }
-          });
+              // Persist too: addFiles stored the record before we knew the path,
+              // so the disk link would otherwise be lost on reload.
+              await fileStorage.updateFileMetadata(file.fileId, {
+                localFilePath,
+              });
+            }),
+          );
 
           console.log(
             `[Desktop] ${loadedFiles.length} opened file(s) added to FileContext`,
diff --git a/frontend/editor/src/desktop/services/desktopFileLink.ts b/frontend/editor/src/desktop/services/desktopFileLink.ts
new file mode 100644
index 0000000000..a0417e8aa7
--- /dev/null
+++ b/frontend/editor/src/desktop/services/desktopFileLink.ts
@@ -0,0 +1,28 @@
+import { invoke, isTauri } from "@tauri-apps/api/core";
+
+// Desktop implementation of the file-link seam. Overrides the core no-op in
+// desktop builds (see @app alias order) so recent files stay tied to disk.
+
+export const desktopFileLinkingSupported = true;
+
+// True if the path still exists on disk. On any error we assume it exists so a
+// transient failure never prunes a valid recent file.
+export async function pathExistsOnDisk(path: string): Promise<boolean> {
+  if (!isTauri()) return true;
+  try {
+    return await invoke<boolean>("path_exists", { path });
+  } catch (error) {
+    console.error("[desktopFileLink] path_exists failed:", error);
+    return true;
+  }
+}
+
+// Reveal the file in Explorer/Finder, highlighting it.
+export async function revealPathInFileManager(path: string): Promise<void> {
+  if (!isTauri()) return;
+  try {
+    await invoke("reveal_in_file_manager", { path });
+  } catch (error) {
+    console.error("[desktopFileLink] reveal_in_file_manager failed:", error);
+  }
+}
diff --git a/frontend/editor/src/desktop/services/recentFileDiskLink.integration.test.ts b/frontend/editor/src/desktop/services/recentFileDiskLink.integration.test.ts
new file mode 100644
index 0000000000..b773d9545f
--- /dev/null
+++ b/frontend/editor/src/desktop/services/recentFileDiskLink.integration.test.ts
@@ -0,0 +1,206 @@
+import { describe, expect, test, vi, beforeEach } from "vitest";
+import "fake-indexeddb/auto";
+
+// Stub ONLY the Tauri OS boundary. Everything below (real fileStorage on a real
+// IndexedDB, the real desktop desktopFileLink seam, the real pruner) runs for
+// real, so this exercises the full disk-linked-recents chain end to end.
+const { existsByPath, invoke } = vi.hoisted(() => ({
+  existsByPath: new Map<string, boolean>(),
+  invoke: vi.fn(async (cmd: string, args?: Record<string, unknown>) => {
+    if (cmd === "path_exists") {
+      return existsByPath.get(args?.path as string) ?? false;
+    }
+    throw new Error(`unexpected command ${cmd}`);
+  }),
+}));
+vi.mock("@tauri-apps/api/core", async (importActual) => {
+  const actual = await importActual<typeof import("@tauri-apps/api/core")>();
+  return { ...actual, isTauri: () => true, invoke };
+});
+
+import { fileStorage } from "@app/services/fileStorage";
+import {
+  pruneMissingRecentFiles,
+  reconcileServerBackedRecents,
+} from "@app/services/pruneMissingRecentFiles";
+import {
+  createStirlingFile,
+  type StirlingFileStub,
+} from "@app/types/fileContext";
+import type { FileId } from "@app/types/file";
+
+async function storeFile(
+  id: string,
+  overrides: Partial<StirlingFileStub> = {},
+): Promise<void> {
+  const file = new File([`data-${id}`], `${id}.pdf`, {
+    type: "application/pdf",
+  });
+  const stirlingFile = createStirlingFile(file, id as FileId);
+  const stub: StirlingFileStub = {
+    id: id as FileId,
+    name: `${id}.pdf`,
+    type: "application/pdf",
+    size: file.size,
+    lastModified: 0,
+    quickKey: stirlingFile.quickKey,
+    isLeaf: true,
+    originalFileId: id,
+    versionNumber: 1,
+    ...overrides,
+  };
+  await fileStorage.storeStirlingFile(stirlingFile, stub);
+}
+
+beforeEach(async () => {
+  existsByPath.clear();
+  invoke.mockClear();
+  // fake-indexeddb persists within a run; wipe the store for test isolation.
+  const all = await fileStorage.getAllStirlingFileStubs();
+  if (all.length > 0) {
+    await fileStorage.deleteMultipleStirlingFiles(all.map((s) => s.id));
+  }
+});
+
+describe("desktop recent files ↔ disk link (real storage + seam)", () => {
+  test("localFilePath round-trips through IndexedDB", async () => {
+    await storeFile("rt", { localFilePath: "/docs/rt.pdf" });
+
+    const stubs = await fileStorage.getLeafStirlingFileStubs();
+    const loaded = stubs.find((s) => s.id === "rt");
+
+    // Regression: before persisting localFilePath in the record, this was
+    // undefined after a reload and the whole feature was inert.
+    expect(loaded?.localFilePath).toBe("/docs/rt.pdf");
+  });
+
+  test("localFilePath applied post-store (OS open-with / drag-drop path) persists", async () => {
+    // useAppInitialization stores the opened file first, then applies the disk
+    // path via updateFileMetadata — this is the drag-drop / "open with" path.
+    await storeFile("dragged");
+    await fileStorage.updateFileMetadata("dragged" as FileId, {
+      localFilePath: "/docs/dragged.pdf",
+    });
+
+    const stubs = await fileStorage.getLeafStirlingFileStubs();
+    expect(stubs.find((s) => s.id === "dragged")?.localFilePath).toBe(
+      "/docs/dragged.pdf",
+    );
+  });
+
+  test("prunes a recent whose disk file is gone and deletes it from storage", async () => {
+    await storeFile("gone", { localFilePath: "/docs/gone.pdf" });
+    await storeFile("kept", { localFilePath: "/docs/kept.pdf" });
+    existsByPath.set("/docs/gone.pdf", false);
+    existsByPath.set("/docs/kept.pdf", true);
+
+    const stubs = await fileStorage.getLeafStirlingFileStubs();
+    const survivors = await pruneMissingRecentFiles(stubs);
+
+    expect(survivors.map((s) => s.id).sort()).toEqual(["kept"]);
+    // Really removed from IndexedDB, not just filtered from the array.
+    expect(await fileStorage.getStirlingFileStub("gone" as FileId)).toBeNull();
+    expect(
+      await fileStorage.getStirlingFileStub("kept" as FileId),
+    ).not.toBeNull();
+    expect(invoke).toHaveBeenCalledWith("path_exists", {
+      path: "/docs/gone.pdf",
+    });
+  });
+
+  test("prune leaves server-backed files alone (server reconciliation owns them)", async () => {
+    await storeFile("onserver", {
+      localFilePath: "/docs/onserver.pdf",
+      remoteStorageId: 42,
+    });
+    existsByPath.set("/docs/onserver.pdf", false);
+
+    const survivors = await pruneMissingRecentFiles(
+      await fileStorage.getLeafStirlingFileStubs(),
+    );
+
+    // Untouched by the pre-fetch prune: still present, link intact.
+    expect(survivors.find((s) => s.id === "onserver")?.localFilePath).toBe(
+      "/docs/onserver.pdf",
+    );
+    expect(
+      await fileStorage.getStirlingFileStub("onserver" as FileId),
+    ).not.toBeNull();
+  });
+
+  test("demotes a server-confirmed file whose disk original is gone (removed locally, kept on server)", async () => {
+    await storeFile("onserver", {
+      localFilePath: "/docs/onserver.pdf",
+      remoteStorageId: 42,
+    });
+    existsByPath.set("/docs/onserver.pdf", false);
+
+    const removed = await reconcileServerBackedRecents(
+      await fileStorage.getLeafStirlingFileStubs(),
+      (id) => id === 42, // server confirms it holds file 42
+    );
+
+    expect(removed).toEqual(["onserver"]);
+    // Local copy really removed from IndexedDB — it becomes a pure server file
+    // (shown under My Files, downloadable), so nothing is lost.
+    expect(
+      await fileStorage.getStirlingFileStub("onserver" as FileId),
+    ).toBeNull();
+  });
+
+  test("does NOT demote a server-backed file the server can't confirm (no data loss)", async () => {
+    await storeFile("stale", {
+      localFilePath: "/docs/stale.pdf",
+      remoteStorageId: 99,
+    });
+    existsByPath.set("/docs/stale.pdf", false);
+
+    const removed = await reconcileServerBackedRecents(
+      await fileStorage.getLeafStirlingFileStubs(),
+      () => false, // server no longer has it
+    );
+
+    expect(removed).toEqual([]);
+    // Local copy preserved — it may be the only remaining copy.
+    expect(
+      await fileStorage.getStirlingFileStub("stale" as FileId),
+    ).not.toBeNull();
+  });
+
+  test("keeps an in-app-edited file whose disk path is gone, detaching the dead link", async () => {
+    // A v2 with tool history: its edited bytes live only in IndexedDB once the
+    // disk file is gone, so it must be KEPT (not deleted) — just detached.
+    await storeFile("edited", {
+      localFilePath: "/docs/edited.pdf",
+      versionNumber: 2,
+      toolHistory: [{ toolId: "compress" as never, timestamp: 1 }],
+    });
+    existsByPath.set("/docs/edited.pdf", false);
+
+    const survivors = await pruneMissingRecentFiles(
+      await fileStorage.getLeafStirlingFileStubs(),
+    );
+
+    expect(survivors.some((s) => s.id === "edited")).toBe(true);
+    const stored = await fileStorage.getStirlingFileStub("edited" as FileId);
+    expect(stored).not.toBeNull();
+    expect(stored?.localFilePath).toBeUndefined();
+  });
+
+  test("leaves web/browser-uploaded files (no disk link) untouched", async () => {
+    // Files added via the <input type=file> fallback have no localFilePath, so
+    // they are never disk-checked, detached, or pruned.
+    await storeFile("weblink");
+    existsByPath.set("/docs/anything.pdf", false);
+
+    const survivors = await pruneMissingRecentFiles(
+      await fileStorage.getLeafStirlingFileStubs(),
+    );
+
+    expect(survivors.some((s) => s.id === "weblink")).toBe(true);
+    expect(
+      await fileStorage.getStirlingFileStub("weblink" as FileId),
+    ).not.toBeNull();
+    expect(invoke).not.toHaveBeenCalled();
+  });
+});