diff --git a/ui/src/components/NewIssueDialog.test.tsx b/ui/src/components/NewIssueDialog.test.tsx
index 5be82be0af9..6290d3f8a82 100644
--- a/ui/src/components/NewIssueDialog.test.tsx
+++ b/ui/src/components/NewIssueDialog.test.tsx
@@ -14,6 +14,7 @@ const dialogState = vi.hoisted(() => ({
 }));
 
 const dialogContentState = vi.hoisted(() => ({
+  onEscapeKeyDown: null as null | ((event: KeyboardEvent) => void),
   onPointerDownOutside: null as null | ((event: {
     detail: { originalEvent: { target: EventTarget | null } };
     preventDefault: () => void;
@@ -193,14 +194,15 @@ vi.mock("@/components/ui/dialog", () => ({
   DialogContent: ({
     children,
     showCloseButton: _showCloseButton,
-    onEscapeKeyDown: _onEscapeKeyDown,
+    onEscapeKeyDown,
     onPointerDownOutside,
     ...props
   }: ComponentProps<"div"> & {
     showCloseButton?: boolean;
-    onEscapeKeyDown?: (event: unknown) => void;
+    onEscapeKeyDown?: (event: KeyboardEvent) => void;
     onPointerDownOutside?: (event: unknown) => void;
   }) => {
+    dialogContentState.onEscapeKeyDown = onEscapeKeyDown ?? null;
     dialogContentState.onPointerDownOutside = onPointerDownOutside as typeof dialogContentState.onPointerDownOutside;
     return <div {...props}>{children}</div>;
   },
@@ -315,6 +317,7 @@ describe("NewIssueDialog", () => {
     dialogState.newIssueOpen = true;
     dialogState.newIssueDefaults = {};
     dialogState.closeNewIssue.mockReset();
+    dialogContentState.onEscapeKeyDown = null;
     dialogContentState.onPointerDownOutside = null;
     toastState.pushToast.mockReset();
     mockIssuesApi.create.mockReset();
@@ -849,7 +852,7 @@ describe("NewIssueDialog", () => {
     await act(async () => {
       modeChip()?.dispatchEvent(new KeyboardEvent("keydown", {
         bubbles: true,
-        code: "Period",
+        code: "",
         key: ".",
         metaKey: true,
       }));
@@ -879,6 +882,63 @@ describe("NewIssueDialog", () => {
     act(() => root.unmount());
   });
 
+  it("cycles work modes when iOS reports cmd-period as Escape", async () => {
+    const { root } = renderDialog(container);
+    await flush();
+
+    const modeChip = () => container.querySelector("[data-issue-work-mode-chip]");
+    expect(modeChip()?.getAttribute("data-issue-work-mode-chip")).toBe("standard");
+    expect(dialogContentState.onEscapeKeyDown).not.toBeNull();
+
+    const commandPeriodAsEscape = new KeyboardEvent("keydown", {
+      bubbles: true,
+      cancelable: true,
+      key: "Escape",
+      metaKey: true,
+    });
+    await act(async () => {
+      dialogContentState.onEscapeKeyDown?.(commandPeriodAsEscape);
+    });
+
+    expect(commandPeriodAsEscape.defaultPrevented).toBe(true);
+    expect(modeChip()?.getAttribute("data-issue-work-mode-chip")).toBe("planning");
+    expect(dialogState.closeNewIssue).not.toHaveBeenCalled();
+
+    const plainEscape = new KeyboardEvent("keydown", {
+      bubbles: true,
+      cancelable: true,
+      key: "Escape",
+    });
+    await act(async () => {
+      dialogContentState.onEscapeKeyDown?.(plainEscape);
+    });
+
+    expect(plainEscape.defaultPrevented).toBe(false);
+    expect(modeChip()?.getAttribute("data-issue-work-mode-chip")).toBe("planning");
+
+    act(() => root.unmount());
+  });
+
+  it("cycles work modes with ctrl-period", async () => {
+    const { root } = renderDialog(container);
+    await flush();
+
+    const modeChip = () => container.querySelector("[data-issue-work-mode-chip]");
+    expect(modeChip()?.getAttribute("data-issue-work-mode-chip")).toBe("standard");
+
+    await act(async () => {
+      modeChip()?.dispatchEvent(new KeyboardEvent("keydown", {
+        bubbles: true,
+        code: "Period",
+        key: ".",
+        ctrlKey: true,
+      }));
+    });
+    expect(modeChip()?.getAttribute("data-issue-work-mode-chip")).toBe("planning");
+
+    act(() => root.unmount());
+  });
+
   it("submits the parent assignee when a sub-issue opens with inherited defaults", async () => {
     dialogState.newIssueDefaults = {
       parentId: "issue-1",
diff --git a/ui/src/components/NewIssueDialog.tsx b/ui/src/components/NewIssueDialog.tsx
index bcbda2d457d..96f0d938576 100644
--- a/ui/src/components/NewIssueDialog.tsx
+++ b/ui/src/components/NewIssueDialog.tsx
@@ -268,6 +268,15 @@ function defaultExecutionWorkspaceModeForIssueDefaults(
     : defaultExecutionWorkspaceModeForProject(project);
 }
 
+function isWorkModePeriodShortcut(e: Pick<React.KeyboardEvent, "code" | "ctrlKey" | "key" | "metaKey">) {
+  const isPeriod = e.code === "Period" || e.key === ".";
+  return (e.metaKey || e.ctrlKey) && isPeriod;
+}
+
+function isWorkModeEscapeShortcut(e: Pick<KeyboardEvent, "ctrlKey" | "key" | "metaKey">) {
+  return (e.metaKey || e.ctrlKey) && e.key === "Escape";
+}
+
 const IssueTitleTextarea = memo(function IssueTitleTextarea({
   value,
   pending,
@@ -1006,7 +1015,7 @@ export function NewIssueDialog() {
   }
 
   function handleKeyDown(e: React.KeyboardEvent) {
-    if ((e.metaKey || e.ctrlKey) && e.code === "Period") {
+    if (isWorkModePeriodShortcut(e)) {
       e.preventDefault();
       setWorkMode((current) => nextWorkMode(current));
       return;
@@ -1236,6 +1245,15 @@ export function NewIssueDialog() {
         )}
         onKeyDown={handleKeyDown}
         onEscapeKeyDown={(event) => {
+          if (event.defaultPrevented) return;
+          // iOS Safari maps command-period to Escape for hardware keyboards.
+          // Treat modifier-Escape as the same mode-cycle shortcut so the
+          // dialog does not dismiss before the shortcut can run.
+          if (isWorkModeEscapeShortcut(event)) {
+            event.preventDefault();
+            setWorkMode((current) => nextWorkMode(current));
+            return;
+          }
           if (createIssue.isPending) {
             event.preventDefault();
           }