diff --git a/apps/web/src/components/files/FilePreviewPanel.tsx b/apps/web/src/components/files/FilePreviewPanel.tsx
index a8c364763c28..8614e7e90f44 100644
--- a/apps/web/src/components/files/FilePreviewPanel.tsx
+++ b/apps/web/src/components/files/FilePreviewPanel.tsx
@@ -404,16 +404,18 @@ function useFileSaveCoordinator({
   environmentId,
   cwd,
   relativePath,
+  contents,
   onPendingChange,
 }: Pick<
   EditableFileSurfaceProps,
-  "environmentId" | "cwd" | "relativePath" | "onPendingChange"
+  "environmentId" | "cwd" | "relativePath" | "contents" | "onPendingChange"
 >): FileSaveCoordinator {
   const writeFile = useAtomCommand(projectEnvironment.writeFile);
   const coordinator = useMemo(
     () =>
       new FileSaveCoordinator({
         debounceMs: FILE_SAVE_DEBOUNCE_MS,
+        initialContents: contents,
         onPendingChange: (pending) => onPendingChange(relativePath, pending),
         persist: (nextContents) =>
           writeFile({
@@ -423,10 +425,31 @@ function useFileSaveCoordinator({
         onConfirmed: (confirmedContents) => {
           confirmProjectFileQueryData(environmentId, cwd, relativePath, confirmedContents);
         },
+        onRollback: ({ failedContents, confirmedContents, result }) => {
+          const overlay = getOptimisticProjectFileQueryData(environmentId, cwd, relativePath);
+          if (overlay !== null && overlay.contents !== failedContents) {
+            onPendingChange(relativePath, true);
+            return;
+          }
+          setProjectFileQueryData(environmentId, cwd, relativePath, confirmedContents);
+          confirmProjectFileQueryData(environmentId, cwd, relativePath, confirmedContents);
+          onPendingChange(relativePath, false);
+          const error = result?._tag === "Failure" ? squashAtomCommandFailure(result) : null;
+          toastManager.add({
+            type: "error",
+            title: "Could not save file",
+            description: error instanceof Error ? error.message : relativePath,
+          });
+        },
       }),
+    // initialContents is the loaded file at mount. Overlay edits must not
+    // rebuild the coordinator or last-confirmed state resets on every keystroke.
     [cwd, environmentId, onPendingChange, relativePath, writeFile],
   );
 
+  useEffect(() => {
+    coordinator.syncConfirmed(contents);
+  }, [contents, coordinator]);
   useEffect(() => () => coordinator.dispose(), [coordinator]);
   return coordinator;
 }
@@ -461,6 +484,7 @@ function EditableFileSurface({
     environmentId,
     cwd,
     relativePath,
+    contents,
     onPendingChange,
   });
   const editor = useMemo(
@@ -722,6 +746,7 @@ function RenderedMarkdownSurface({
     environmentId,
     cwd,
     relativePath,
+    contents,
     onPendingChange,
   });
 
diff --git a/apps/web/src/components/files/fileSaveCoordinator.test.ts b/apps/web/src/components/files/fileSaveCoordinator.test.ts
index 1acbb0c1d205..4d0c56e8e76a 100644
--- a/apps/web/src/components/files/fileSaveCoordinator.test.ts
+++ b/apps/web/src/components/files/fileSaveCoordinator.test.ts
@@ -27,9 +27,11 @@ describe("FileSaveCoordinator", () => {
     const onConfirmed = vi.fn();
     const coordinator = new FileSaveCoordinator({
       debounceMs: 500,
+      initialContents: "disk",
       persist,
       onPendingChange,
       onConfirmed,
+      onRollback: vi.fn(),
     });
 
     coordinator.change("first");
@@ -55,9 +57,11 @@ describe("FileSaveCoordinator", () => {
     const onPendingChange = vi.fn();
     const coordinator = new FileSaveCoordinator({
       debounceMs: 500,
+      initialContents: "disk",
       persist,
       onPendingChange,
       onConfirmed: vi.fn(),
+      onRollback: vi.fn(),
     });
 
     coordinator.change("first");
@@ -73,22 +77,185 @@ describe("FileSaveCoordinator", () => {
     expect(onPendingChange.mock.calls.at(-1)).toEqual([false]);
   });
 
-  it("leaves the file pending when the latest write fails", async () => {
+  it("rolls back to the last confirmed contents when the latest write fails", async () => {
     vi.useFakeTimers();
     const onPendingChange = vi.fn();
+    const onRollback = vi.fn();
+    const failure = AsyncResult.failure(Cause.fail(new Error("write failed")));
     const coordinator = new FileSaveCoordinator({
       debounceMs: 500,
+      initialContents: "disk",
+      persist: vi.fn().mockResolvedValue(failure),
+      onPendingChange,
+      onConfirmed: vi.fn(),
+      onRollback,
+    });
+
+    coordinator.change("latest");
+    await vi.advanceTimersByTimeAsync(500);
+    await Promise.resolve();
+    expect(onRollback).toHaveBeenCalledWith({
+      failedContents: "latest",
+      confirmedContents: "disk",
+      result: failure,
+    });
+    expect(onPendingChange).not.toHaveBeenCalledWith(false);
+  });
+
+  it("does not roll back a newer edit when an older write fails", async () => {
+    vi.useFakeTimers();
+    const firstWrite = deferred();
+    const persist = vi
+      .fn<(contents: string) => Promise<AtomCommandResult<void, never>>>()
+      .mockReturnValueOnce(firstWrite.promise)
+      .mockResolvedValueOnce(AsyncResult.success(undefined));
+    const onRollback = vi.fn();
+    const onConfirmed = vi.fn();
+    const coordinator = new FileSaveCoordinator({
+      debounceMs: 500,
+      initialContents: "disk",
+      persist,
+      onPendingChange: vi.fn(),
+      onConfirmed,
+      onRollback,
+    });
+
+    coordinator.change("first");
+    await vi.advanceTimersByTimeAsync(500);
+    coordinator.change("latest");
+    firstWrite.resolve(AsyncResult.failure(Cause.fail(new Error("write failed"))));
+    await vi.runAllTimersAsync();
+
+    expect(onRollback).not.toHaveBeenCalled();
+    expect(persist).toHaveBeenLastCalledWith("latest");
+    expect(onConfirmed).toHaveBeenCalledWith("latest");
+  });
+
+  it("does not roll back an interrupted write", async () => {
+    vi.useFakeTimers();
+    const onRollback = vi.fn();
+    const onPendingChange = vi.fn();
+    const coordinator = new FileSaveCoordinator({
+      debounceMs: 500,
+      initialContents: "disk",
+      persist: vi.fn().mockResolvedValue(AsyncResult.failure(Cause.interrupt(1))),
+      onPendingChange,
+      onConfirmed: vi.fn(),
+      onRollback,
+    });
+
+    coordinator.change("latest");
+    await vi.advanceTimersByTimeAsync(500);
+    await Promise.resolve();
+    expect(onRollback).not.toHaveBeenCalled();
+    expect(onPendingChange).not.toHaveBeenCalledWith(false);
+  });
+
+  it("still rolls back a failed write that finishes after dispose", async () => {
+    vi.useFakeTimers();
+    const write = deferred();
+    const onRollback = vi.fn();
+    const onPendingChange = vi.fn();
+    const failure = AsyncResult.failure(Cause.fail(new Error("write failed")));
+    const coordinator = new FileSaveCoordinator({
+      debounceMs: 500,
+      initialContents: "disk",
+      persist: vi.fn().mockReturnValue(write.promise),
+      onPendingChange,
+      onConfirmed: vi.fn(),
+      onRollback,
+    });
+
+    coordinator.change("latest");
+    await vi.advanceTimersByTimeAsync(500);
+    coordinator.dispose();
+    write.resolve(failure);
+    await Promise.resolve();
+    expect(onRollback).toHaveBeenCalledWith({
+      failedContents: "latest",
+      confirmedContents: "disk",
+      result: failure,
+    });
+    expect(onPendingChange).not.toHaveBeenCalledWith(false);
+  });
+
+  it("does not persist a discarded failed edit on dispose", async () => {
+    vi.useFakeTimers();
+    const persist = vi
+      .fn<(contents: string) => Promise<AtomCommandResult<void, never>>>()
+      .mockResolvedValue(AsyncResult.failure(Cause.fail(new Error("write failed"))));
+    const coordinator = new FileSaveCoordinator({
+      debounceMs: 500,
+      initialContents: "disk",
+      persist,
+      onPendingChange: vi.fn(),
+      onConfirmed: vi.fn(),
+      onRollback: vi.fn(),
+    });
+
+    coordinator.change("latest");
+    await vi.advanceTimersByTimeAsync(500);
+    await Promise.resolve();
+    expect(persist).toHaveBeenCalledOnce();
+    coordinator.dispose();
+    await Promise.resolve();
+    expect(persist).toHaveBeenCalledOnce();
+  });
+
+  it("uses a later confirmed refresh as the rollback baseline", async () => {
+    vi.useFakeTimers();
+    const onRollback = vi.fn();
+    const coordinator = new FileSaveCoordinator({
+      debounceMs: 500,
+      initialContents: "disk",
       persist: vi
         .fn()
         .mockResolvedValue(AsyncResult.failure(Cause.fail(new Error("write failed")))),
-      onPendingChange,
+      onPendingChange: vi.fn(),
       onConfirmed: vi.fn(),
+      onRollback,
     });
 
+    coordinator.syncConfirmed("refreshed");
     coordinator.change("latest");
     await vi.advanceTimersByTimeAsync(500);
     await Promise.resolve();
-    expect(onPendingChange).toHaveBeenCalledWith(true);
-    expect(onPendingChange).not.toHaveBeenCalledWith(false);
+    expect(onRollback).toHaveBeenCalledWith(
+      expect.objectContaining({
+        failedContents: "latest",
+        confirmedContents: "refreshed",
+      }),
+    );
+  });
+
+  it("lets idle refreshes update the baseline after a successful save", async () => {
+    vi.useFakeTimers();
+    const persist = vi
+      .fn<(contents: string) => Promise<AtomCommandResult<void, never>>>()
+      .mockResolvedValueOnce(AsyncResult.success(undefined))
+      .mockResolvedValueOnce(AsyncResult.failure(Cause.fail(new Error("write failed"))));
+    const onRollback = vi.fn();
+    const coordinator = new FileSaveCoordinator({
+      debounceMs: 500,
+      initialContents: "disk",
+      persist,
+      onPendingChange: vi.fn(),
+      onConfirmed: vi.fn(),
+      onRollback,
+    });
+
+    coordinator.change("saved");
+    await vi.advanceTimersByTimeAsync(500);
+    await Promise.resolve();
+    coordinator.syncConfirmed("refreshed");
+    coordinator.change("latest");
+    await vi.advanceTimersByTimeAsync(500);
+    await Promise.resolve();
+    expect(onRollback).toHaveBeenCalledWith(
+      expect.objectContaining({
+        failedContents: "latest",
+        confirmedContents: "refreshed",
+      }),
+    );
   });
 });
diff --git a/apps/web/src/components/files/fileSaveCoordinator.ts b/apps/web/src/components/files/fileSaveCoordinator.ts
index 138f01d360e3..753fded6fff2 100644
--- a/apps/web/src/components/files/fileSaveCoordinator.ts
+++ b/apps/web/src/components/files/fileSaveCoordinator.ts
@@ -1,21 +1,35 @@
-import type { AtomCommandResult } from "@t3tools/client-runtime/state/runtime";
+import {
+  type AtomCommandResult,
+  isAtomCommandInterrupted,
+} from "@t3tools/client-runtime/state/runtime";
+
+export interface FileSaveRollback<A = unknown, E = unknown> {
+  readonly failedContents: string;
+  readonly confirmedContents: string;
+  readonly result: AtomCommandResult<A, E> | null;
+}
 
 export interface FileSaveCoordinatorOptions<A, E> {
   readonly debounceMs: number;
+  readonly initialContents: string;
   readonly persist: (contents: string) => Promise<AtomCommandResult<A, E>>;
   readonly onPendingChange: (pending: boolean) => void;
   readonly onConfirmed: (contents: string) => void;
+  readonly onRollback: (rollback: FileSaveRollback<A, E>) => void;
 }
 
 export class FileSaveCoordinator<A = unknown, E = unknown> {
   private timer: ReturnType<typeof setTimeout> | null = null;
   private latestContents = "";
+  private lastConfirmedContents: string;
   private latestRevision = 0;
   private lastChangeAt = 0;
   private saving = false;
   private disposed = false;
 
-  constructor(private readonly options: FileSaveCoordinatorOptions<A, E>) {}
+  constructor(private readonly options: FileSaveCoordinatorOptions<A, E>) {
+    this.lastConfirmedContents = options.initialContents;
+  }
 
   change(contents: string): void {
     this.latestContents = contents;
@@ -25,6 +39,12 @@ export class FileSaveCoordinator<A = unknown, E = unknown> {
     this.schedule(this.options.debounceMs);
   }
 
+  syncConfirmed(contents: string): void {
+    if (this.latestRevision === 0 && !this.saving) {
+      this.lastConfirmedContents = contents;
+    }
+  }
+
   dispose(): void {
     this.disposed = true;
     this.clearTimer();
@@ -51,15 +71,39 @@ export class FileSaveCoordinator<A = unknown, E = unknown> {
     this.saving = true;
     const contents = this.latestContents;
     const revision = this.latestRevision;
-    const result = await this.options.persist(contents);
-    const succeeded = result._tag === "Success";
-    if (succeeded) {
-      this.options.onConfirmed(contents);
+    let result: AtomCommandResult<A, E> | null = null;
+    let succeeded = false;
+    let interrupted = false;
+    try {
+      result = await this.options.persist(contents);
+      succeeded = result._tag === "Success";
+      interrupted = !succeeded && isAtomCommandInterrupted(result);
+      if (succeeded) {
+        this.lastConfirmedContents = contents;
+        this.options.onConfirmed(contents);
+      }
+    } catch {
+      succeeded = false;
+      interrupted = false;
     }
 
     this.saving = false;
     if (revision === this.latestRevision) {
-      if (succeeded) this.options.onPendingChange(false);
+      if (interrupted) {
+        return;
+      }
+      if (!succeeded) {
+        this.latestRevision = 0;
+        this.latestContents = this.lastConfirmedContents;
+        this.options.onRollback({
+          failedContents: contents,
+          confirmedContents: this.lastConfirmedContents,
+          result,
+        });
+        return;
+      }
+      this.latestRevision = 0;
+      if (!this.disposed) this.options.onPendingChange(false);
       return;
     }