diff --git a/packages/app/e2e/rewind-menu.ui-contract.spec.ts b/packages/app/e2e/rewind-menu.ui-contract.spec.ts
index e6c74bcf8..3f0ebfb64 100644
--- a/packages/app/e2e/rewind-menu.ui-contract.spec.ts
+++ b/packages/app/e2e/rewind-menu.ui-contract.spec.ts
@@ -68,7 +68,6 @@ test.describe("Rewind sheet", () => {
       await page.getByTestId("rewind-menu-trigger").first().click();
       const rewindSheet = page.getByTestId("rewind-menu-content");
       await expect(rewindSheet).toBeVisible();
-      await expect(rewindSheet.getByText("Rewind to this message", { exact: true })).toBeVisible();
       await expect(
         rewindSheet.getByText("This action cannot be undone", { exact: true }),
       ).toBeVisible();
@@ -149,7 +148,6 @@ test.describe("Rewind sheet", () => {
       await page.getByTestId("rewind-menu-trigger").first().click();
       const rewindSheet = page.getByTestId("rewind-menu-content");
       await expect(rewindSheet).toBeVisible();
-      await expect(rewindSheet.getByText("Rewind to this message", { exact: true })).toBeVisible();
       await expect(
         rewindSheet.getByText("This action cannot be undone", { exact: true }),
       ).toBeVisible();
diff --git a/packages/app/src/components/message.tsx b/packages/app/src/components/message.tsx
index 344992c0f..fd1300740 100644
--- a/packages/app/src/components/message.tsx
+++ b/packages/app/src/components/message.tsx
@@ -409,8 +409,14 @@ const userMessageStylesheet = StyleSheet.create((theme) => ({
     fontSize: theme.fontSize.sm,
   },
   copyButton: {
-    padding: theme.spacing[1],
+    alignSelf: "center",
+    width: 24,
+    height: 24,
+    padding: 0,
+    margin: 0,
     marginRight: -theme.spacing[1],
+    alignItems: "center",
+    justifyContent: "center",
   },
   trailingRow: {
     alignSelf: "flex-end",
diff --git a/packages/app/src/components/rewind/rewind-menu.tsx b/packages/app/src/components/rewind/rewind-menu.tsx
index b28686271..05db2900d 100644
--- a/packages/app/src/components/rewind/rewind-menu.tsx
+++ b/packages/app/src/components/rewind/rewind-menu.tsx
@@ -1,15 +1,16 @@
-import { memo, useCallback, useMemo, useState, type ComponentType } from "react";
+import { memo, useCallback, useMemo, useState, type ReactElement } from "react";
 import { Text, View } from "react-native";
 import { FileText, Layers, MessageSquare, Undo2 } from "lucide-react-native";
-import { StyleSheet } from "react-native-unistyles";
-import { AdaptiveModalSheet, type SheetHeader } from "@/components/adaptive-modal-sheet";
-import { Button } from "@/components/ui/button";
-import { Tooltip, TooltipContent, TooltipTrigger } from "@/components/ui/tooltip";
+import { StyleSheet, useUnistyles } from "react-native-unistyles";
 import {
-  type RewindMenuItem,
-  type RewindMode,
-  useRewindCapabilities,
-} from "./use-rewind-capabilities";
+  DropdownMenu,
+  DropdownMenuContent,
+  DropdownMenuItem,
+  DropdownMenuSeparator,
+  DropdownMenuTrigger,
+} from "@/components/ui/dropdown-menu";
+import { Tooltip, TooltipContent, TooltipTrigger } from "@/components/ui/tooltip";
+import { type RewindMode, useRewindCapabilities } from "./use-rewind-capabilities";
 import type { AgentCapabilityFlags } from "@server/server/agent/agent-sdk-types";
 
 export type { RewindMode };
@@ -22,17 +23,14 @@ interface RewindMenuProps {
   testID?: string;
 }
 
-const REWIND_HEADER: SheetHeader = { title: "Rewind to this message" };
-const SNAP_POINTS: string[] = ["42%", "72%"];
-
-function iconForItem(item: RewindMenuItem): ComponentType<{ color: string; size: number }> {
-  switch (item.mode) {
+function getIcon(mode: RewindMode, color: string): ReactElement {
+  switch (mode) {
     case "conversation":
-      return MessageSquare;
+      return <MessageSquare size={16} color={color} />;
     case "files":
-      return FileText;
+      return <FileText size={16} color={color} />;
     case "both":
-      return Layers;
+      return <Layers size={16} color={color} />;
   }
 }
 
@@ -40,36 +38,44 @@ export const RewindMenu = memo(function RewindMenu({
   capabilities,
   rewoundText,
   onRewind,
-  isPending = false,
+  isPending: isPendingProp = false,
   testID = "rewind-menu",
 }: RewindMenuProps) {
+  const { theme } = useUnistyles();
   const items = useRewindCapabilities(capabilities);
-  const [isSheetVisible, setIsSheetVisible] = useState(false);
+  const [isOpen, setIsOpen] = useState(false);
   const [pendingMode, setPendingMode] = useState<RewindMode | null>(null);
-  const handleOpen = useCallback(() => setIsSheetVisible(true), []);
-  const handleClose = useCallback(() => {
-    if (!isPending) {
-      setIsSheetVisible(false);
-    }
-  }, [isPending]);
+  const isLocked = isPendingProp || pendingMode !== null;
+
+  const handleOpenChange = useCallback(
+    (next: boolean) => {
+      if (!next && pendingMode !== null) return;
+      setIsOpen(next);
+    },
+    [pendingMode],
+  );
+
   const handleSelect = useCallback(
     (mode: RewindMode) => async () => {
-      if (isPending) {
-        return;
-      }
+      if (isLocked) return;
       setPendingMode(mode);
       try {
         await onRewind({ mode, rewoundText });
+        setIsOpen(false);
       } catch {
-        // useRewindAgentMutation owns the toast; the sheet only owns flow state.
+        // useRewindAgentMutation owns the toast; the menu only owns flow state.
       } finally {
         setPendingMode(null);
-        setIsSheetVisible(false);
       }
     },
-    [isPending, onRewind, rewoundText],
+    [isLocked, onRewind, rewoundText],
   );
-  const triggerIcon = useCallback((color: string) => <Undo2 size={16} color={color} />, []);
+
+  const triggerStyle = useCallback(
+    () => [styles.trigger, isLocked ? styles.triggerDisabled : null],
+    [isLocked],
+  );
+
   const tooltipContent = useMemo(
     () => (
       <TooltipContent side="top" align="center" offset={8}>
@@ -84,53 +90,48 @@ export const RewindMenu = memo(function RewindMenu({
   }
 
   return (
-    <>
-      <Tooltip delayDuration={0} enabledOnDesktop enabledOnMobile={false}>
+    <DropdownMenu open={isOpen} onOpenChange={handleOpenChange}>
+      <Tooltip delayDuration={250} enabledOnDesktop enabledOnMobile={false}>
         <TooltipTrigger asChild>
-          <Button
-            accessibilityLabel="Rewind to this message"
-            disabled={isPending}
-            leftIcon={triggerIcon}
-            onPress={handleOpen}
-            size="xs"
-            style={styles.trigger}
-            testID={`${testID}-trigger`}
-            variant="ghost"
-          />
+          <View style={styles.triggerSlot} collapsable={false}>
+            <DropdownMenuTrigger
+              accessibilityLabel="Rewind to this message"
+              accessibilityRole="button"
+              disabled={isLocked}
+              style={triggerStyle}
+              testID={`${testID}-trigger`}
+            >
+              {({ hovered, open }) => (
+                <Undo2
+                  size={16}
+                  color={hovered || open ? theme.colors.foreground : theme.colors.foregroundMuted}
+                />
+              )}
+            </DropdownMenuTrigger>
+          </View>
         </TooltipTrigger>
         {tooltipContent}
       </Tooltip>
-      <AdaptiveModalSheet
-        desktopMaxWidth={420}
-        header={REWIND_HEADER}
-        onClose={handleClose}
-        scrollable={false}
-        snapPoints={SNAP_POINTS}
-        testID={`${testID}-content`}
-        visible={isSheetVisible}
-      >
-        <View style={styles.content}>
+      <DropdownMenuContent align="end" minWidth={220} side="bottom" testID={`${testID}-content`}>
+        <View style={styles.warningHeader}>
           <Text style={styles.warningText}>This action cannot be undone</Text>
-          <View style={styles.actions}>
-            {items.map((item) => (
-              <Button
-                key={item.mode}
-                leftIcon={iconForItem(item)}
-                loading={pendingMode === item.mode}
-                disabled={isPending}
-                onPress={handleSelect(item.mode)}
-                size="md"
-                style={styles.actionButton}
-                testID={item.testID}
-                variant="secondary"
-              >
-                {item.label}
-              </Button>
-            ))}
-          </View>
         </View>
-      </AdaptiveModalSheet>
-    </>
+        <DropdownMenuSeparator />
+        {items.map((item) => (
+          <DropdownMenuItem
+            key={item.mode}
+            closeOnSelect={false}
+            disabled={isLocked && pendingMode !== item.mode}
+            leading={getIcon(item.mode, theme.colors.foreground)}
+            onSelect={handleSelect(item.mode)}
+            status={pendingMode === item.mode ? "pending" : undefined}
+            testID={item.testID}
+          >
+            {item.label}
+          </DropdownMenuItem>
+        ))}
+      </DropdownMenuContent>
+    </DropdownMenu>
   );
 });
 
@@ -138,27 +139,27 @@ const styles = StyleSheet.create((theme) => ({
   trigger: {
     width: 24,
     height: 24,
-    minHeight: 24,
-    paddingHorizontal: 0,
-    paddingVertical: 0,
     alignItems: "center",
     justifyContent: "center",
+    backgroundColor: "transparent",
+  },
+  triggerDisabled: {
+    opacity: theme.opacity[50],
+  },
+  triggerSlot: {
+    alignSelf: "flex-start",
   },
   tooltipText: {
     color: theme.colors.foreground,
     fontSize: theme.fontSize.xs,
   },
-  content: {
-    gap: theme.spacing[4],
+  warningHeader: {
+    paddingHorizontal: theme.spacing[3],
+    paddingTop: theme.spacing[2],
+    paddingBottom: theme.spacing[2],
   },
   warningText: {
-    color: theme.colors.statusWarning,
-    fontSize: theme.fontSize.sm,
-  },
-  actions: {
-    gap: theme.spacing[2],
-  },
-  actionButton: {
-    justifyContent: "flex-start",
+    color: theme.colors.foregroundMuted,
+    fontSize: theme.fontSize.xs,
   },
 }));