diff --git a/packages/app/e2e/browser/claude-bypass-permissions.real.spec.ts b/packages/app/e2e/browser/claude-bypass-permissions.real.spec.ts
new file mode 100644
index 0000000000..5d65c7e5a8
--- /dev/null
+++ b/packages/app/e2e/browser/claude-bypass-permissions.real.spec.ts
@@ -0,0 +1,83 @@
+import {
+  existsSync,
+  mkdirSync,
+  mkdtempSync,
+  readFileSync,
+  realpathSync,
+  writeFileSync,
+} from "node:fs";
+import { tmpdir } from "node:os";
+import path from "node:path";
+import { expect, test } from "../support/fixtures";
+import { submitMessage } from "../support/helpers/composer";
+import { cleanupRewindFlow, type AgentHandle, launchAgent } from "../support/helpers/rewind-flow";
+
+const FILE_NAME = "BYPASS.md";
+const FILE_CONTENT = "PASEO_BYPASS_PLAYWRIGHT_OK\n";
+const COMPLETION = "BYPASS_WRITE_COMPLETE";
+
+function configureClaudeToAskForFileTools(handle: AgentHandle): void {
+  const settingsDirectory = path.join(handle.cwd, ".claude");
+  mkdirSync(settingsDirectory);
+  writeFileSync(
+    path.join(settingsDirectory, "settings.local.json"),
+    `${JSON.stringify({ permissions: { ask: ["Bash", "Write", "Edit"] } }, null, 2)}\n`,
+  );
+}
+
+async function switchClaudeToBypassPermissions(handle: AgentHandle): Promise<void> {
+  const modeControl = handle.page.getByRole("button", { name: /^Select agent mode \(/ });
+  await expect(modeControl).toHaveAccessibleName("Select agent mode (Always ask)");
+  await modeControl.click();
+
+  const modePicker = handle.page.getByTestId("combobox-desktop-container").last();
+  await expect(modePicker).toBeVisible();
+  await modePicker.getByText("Bypass", { exact: true }).click();
+  await expect(modeControl).toHaveAccessibleName("Select agent mode (Bypass)");
+}
+
+async function askClaudeToWriteWithoutApproval(handle: AgentHandle): Promise<void> {
+  await submitMessage(
+    handle.page,
+    `Call the Write tool exactly once to create ${FILE_NAME} with exactly ${JSON.stringify(
+      FILE_CONTENT,
+    )}. Do not use Bash or another tool. After Write succeeds, reply exactly ${COMPLETION}.`,
+  );
+}
+
+async function expectBypassWriteToComplete(handle: AgentHandle): Promise<void> {
+  await expect(
+    handle.page.getByTestId("assistant-message").filter({ hasText: COMPLETION }).last(),
+  ).toBeVisible({ timeout: 120_000 });
+  await expect(handle.page.getByTestId("permission-request-question")).toHaveCount(0);
+  await expect.poll(() => existsSync(path.join(handle.cwd, FILE_NAME))).toBe(true);
+  await expect
+    .poll(() => readFileSync(path.join(handle.cwd, FILE_NAME), "utf8"))
+    .toBe(FILE_CONTENT);
+}
+
+test.describe("real Claude bypass permissions", () => {
+  test.setTimeout(240_000);
+
+  test("honors Bypass when project policy asks to approve Write", async ({ page }, testInfo) => {
+    const cwd = realpathSync(mkdtempSync(path.join(tmpdir(), "paseo-claude-bypass-")));
+    let handle: AgentHandle | undefined;
+
+    try {
+      handle = await launchAgent({
+        page,
+        provider: "claude",
+        cwd,
+        mode: "full-access",
+        providerConfig: { modeId: "default" },
+      });
+      configureClaudeToAskForFileTools(handle);
+      await switchClaudeToBypassPermissions(handle);
+      await askClaudeToWriteWithoutApproval(handle);
+      await expectBypassWriteToComplete(handle);
+      await page.screenshot({ path: testInfo.outputPath("claude-bypass-write-complete.png") });
+    } finally {
+      await cleanupRewindFlow({ handle, cwd });
+    }
+  });
+});
diff --git a/packages/server/src/server/agent/providers/claude/agent.ts b/packages/server/src/server/agent/providers/claude/agent.ts
index fb9726e127..7b2ed75499 100644
--- a/packages/server/src/server/agent/providers/claude/agent.ts
+++ b/packages/server/src/server/agent/providers/claude/agent.ts
@@ -4571,9 +4571,23 @@ class ClaudeAgentSession implements AgentSession {
     input,
     options,
   ): Promise<PermissionResult> => {
-    const requestId = `permission-${randomUUID()}`;
     const kind = resolvePermissionKind(toolName, input);
     const requestInput = normalizeClaudeAskUserQuestionRequestInput(toolName, input);
+
+    // Supplying canUseTool gives Paseo a host UI for interactive modes, but the SDK can
+    // still call it for ordinary tools while bypassPermissions is active. Honor the mode
+    // contract here so a Bypass session never turns Write/Bash into a blocking UI card.
+    // A human steer keeps precedence: tools from the superseded turn must be denied until
+    // Claude consumes the steer instead of being allowed to race it.
+    if (
+      kind === "tool" &&
+      this.currentMode === "bypassPermissions" &&
+      this.permissionClearingSteerUuids.size === 0
+    ) {
+      return { behavior: "allow", updatedInput: input };
+    }
+
+    const requestId = `permission-${randomUUID()}`;
     const metadata: AgentMetadata = {};
     if (options.toolUseID) {
       metadata.toolUseId = options.toolUseID;