diff --git a/docs/AGENTS.md b/docs/AGENTS.md
index 76fc25e88a..9d95eddfe6 100644
--- a/docs/AGENTS.md
+++ b/docs/AGENTS.md
@@ -108,6 +108,7 @@ Avoid mock-heavy tests that verify implementation details rather than behavior.
 - Let types drive design: prefer discriminated unions for state, minimize runtime checks, and simplify when types feel unwieldy.
 - Use `using` declarations (or equivalent disposables) for processes, file handles, etc., to ensure cleanup even on errors.
 - Centralize magic constants under `src/constants/`; share them instead of duplicating values across layers.
+- Never repeat constant values (like keybinds) in comments—they become stale when the constant changes.
 
 ## Component State & Storage
 
diff --git a/scripts/bump_tag.sh b/scripts/bump_tag.sh
index 069cf9fddd..db16e557a0 100755
--- a/scripts/bump_tag.sh
+++ b/scripts/bump_tag.sh
@@ -18,7 +18,7 @@ if [[ -z "$CURRENT_VERSION" || "$CURRENT_VERSION" == "null" ]]; then
 fi
 
 # Parse semver components
-IFS='.' read -r MAJOR MINOR_V PATCH <<< "$CURRENT_VERSION"
+IFS='.' read -r MAJOR MINOR_V PATCH <<<"$CURRENT_VERSION"
 
 # Calculate new version
 if [[ "$MINOR" == "true" ]]; then
@@ -30,7 +30,7 @@ fi
 echo "Bumping version: $CURRENT_VERSION -> $NEW_VERSION"
 
 # Update package.json
-jq --arg v "$NEW_VERSION" '.version = $v' package.json > package.json.tmp
+jq --arg v "$NEW_VERSION" '.version = $v' package.json >package.json.tmp
 mv package.json.tmp package.json
 
 # Commit and tag
diff --git a/src/browser/components/ChatInput/index.tsx b/src/browser/components/ChatInput/index.tsx
index c2f6eb5d61..d31db998ef 100644
--- a/src/browser/components/ChatInput/index.tsx
+++ b/src/browser/components/ChatInput/index.tsx
@@ -148,6 +148,25 @@ export const ChatInput: React.FC<ChatInputProps> = (props) => {
   }, []);
   const inputRef = useRef<HTMLTextAreaElement>(null);
   const modelSelectorRef = useRef<ModelSelectorRef>(null);
+
+  // Draft state combines text input and image attachments
+  // Use these helpers to avoid accidentally losing images when modifying text
+  interface DraftState {
+    text: string;
+    images: ImageAttachment[];
+  }
+  const getDraft = useCallback(
+    (): DraftState => ({ text: input, images: imageAttachments }),
+    [input, imageAttachments]
+  );
+  const setDraft = useCallback(
+    (draft: DraftState) => {
+      setInput(draft.text);
+      setImageAttachments(draft.images);
+    },
+    [setInput]
+  );
+  const preEditDraftRef = useRef<DraftState>({ text: "", images: [] });
   const [mode, setMode] = useMode();
   const { recentModels, addModel, defaultModel, setDefaultModel } = useModelLRU();
   const commandListId = useId();
@@ -346,10 +365,11 @@ export const ChatInput: React.FC<ChatInputProps> = (props) => {
     };
   }, [focusMessageInput]);
 
-  // When entering editing mode, populate input with message content
+  // When entering editing mode, save current draft and populate with message content
   useEffect(() => {
     if (editingMessage) {
-      setInput(editingMessage.content);
+      preEditDraftRef.current = getDraft();
+      setDraft({ text: editingMessage.content, images: [] });
       // Auto-resize textarea and focus
       setTimeout(() => {
         if (inputRef.current) {
@@ -360,7 +380,8 @@ export const ChatInput: React.FC<ChatInputProps> = (props) => {
         }
       }, 0);
     }
-  }, [editingMessage, setInput]);
+    // eslint-disable-next-line react-hooks/exhaustive-deps -- only run when editingMessage changes
+  }, [editingMessage]);
 
   // Watch input for slash commands
   useEffect(() => {
@@ -826,6 +847,15 @@ export const ChatInput: React.FC<ChatInputProps> = (props) => {
     }
   };
 
+  // Handler for Escape in vim normal mode - cancels edit if editing
+  const handleEscapeInNormalMode = () => {
+    if (variant === "workspace" && editingMessage && props.onCancelEdit) {
+      setDraft(preEditDraftRef.current);
+      props.onCancelEdit();
+      inputRef.current?.blur();
+    }
+  };
+
   const handleKeyDown = (e: React.KeyboardEvent) => {
     // Handle cancel for creation variant
     if (variant === "creation" && matchesKeybind(e, KEYBINDS.CANCEL) && props.onCancel) {
@@ -870,10 +900,13 @@ export const ChatInput: React.FC<ChatInputProps> = (props) => {
       return;
     }
 
-    // Handle cancel edit (Ctrl+Q) - workspace only
+    // Handle cancel edit (Escape) - workspace only
+    // In vim mode, escape first goes to normal mode; escapeInNormalMode callback handles cancel
+    // In non-vim mode, escape directly cancels edit
     if (matchesKeybind(e, KEYBINDS.CANCEL_EDIT)) {
-      if (variant === "workspace" && editingMessage && props.onCancelEdit) {
+      if (variant === "workspace" && editingMessage && props.onCancelEdit && !vimEnabled) {
         e.preventDefault();
+        setDraft(preEditDraftRef.current);
         props.onCancelEdit();
         const isFocused = document.activeElement === inputRef.current;
         if (isFocused) {
@@ -897,7 +930,6 @@ export const ChatInput: React.FC<ChatInputProps> = (props) => {
     }
 
     // Note: ESC handled by VimTextArea (for mode transitions) and CommandSuggestions (for dismissal)
-    // Edit canceling is Ctrl+Q, stream interruption is Ctrl+C (vim) or Esc (normal)
 
     // Don't handle keys if command suggestions are visible
     if (
@@ -924,7 +956,10 @@ export const ChatInput: React.FC<ChatInputProps> = (props) => {
 
     // Workspace variant placeholders
     if (editingMessage) {
-      return `Edit your message... (${formatKeybind(KEYBINDS.CANCEL_EDIT)} to cancel, ${formatKeybind(KEYBINDS.SEND_MESSAGE)} to send)`;
+      const cancelHint = vimEnabled
+        ? `${formatKeybind(KEYBINDS.CANCEL_EDIT)}×2 to cancel`
+        : `${formatKeybind(KEYBINDS.CANCEL_EDIT)} to cancel`;
+      return `Edit your message... (${cancelHint}, ${formatKeybind(KEYBINDS.SEND_MESSAGE)} to send)`;
     }
     if (isCompacting) {
       const interruptKeybind = vimEnabled
@@ -1040,6 +1075,7 @@ export const ChatInput: React.FC<ChatInputProps> = (props) => {
                   onPaste={handlePaste}
                   onDragOver={handleDragOver}
                   onDrop={handleDrop}
+                  onEscapeInNormalMode={handleEscapeInNormalMode}
                   suppressKeys={showCommandSuggestions ? COMMAND_SUGGESTION_KEYS : undefined}
                   placeholder={placeholder}
                   disabled={!editingMessage && (disabled || isSending)}
@@ -1074,7 +1110,8 @@ export const ChatInput: React.FC<ChatInputProps> = (props) => {
             {/* Editing indicator - workspace only */}
             {variant === "workspace" && editingMessage && (
               <div className="text-edit-mode text-[11px] font-medium">
-                Editing message ({formatKeybind(KEYBINDS.CANCEL_EDIT)} to cancel)
+                Editing message ({formatKeybind(KEYBINDS.CANCEL_EDIT)}
+                {vimEnabled ? "×2" : ""} to cancel)
               </div>
             )}
 
diff --git a/src/browser/components/VimTextArea.tsx b/src/browser/components/VimTextArea.tsx
index 1abcfa0c5a..227a2244c3 100644
--- a/src/browser/components/VimTextArea.tsx
+++ b/src/browser/components/VimTextArea.tsx
@@ -32,12 +32,27 @@ export interface VimTextAreaProps
   isEditing?: boolean;
   suppressKeys?: string[]; // keys for which Vim should not interfere (e.g. ["Tab","ArrowUp","ArrowDown","Escape"]) when popovers are open
   trailingAction?: React.ReactNode;
+  /** Called when Escape is pressed in normal mode (vim) - useful for cancel edit */
+  onEscapeInNormalMode?: () => void;
 }
 
 type VimMode = vim.VimMode;
 
 export const VimTextArea = React.forwardRef<HTMLTextAreaElement, VimTextAreaProps>(
-  ({ value, onChange, mode, isEditing, suppressKeys, onKeyDown, trailingAction, ...rest }, ref) => {
+  (
+    {
+      value,
+      onChange,
+      mode,
+      isEditing,
+      suppressKeys,
+      onKeyDown,
+      trailingAction,
+      onEscapeInNormalMode,
+      ...rest
+    },
+    ref
+  ) => {
     const textareaRef = useRef<HTMLTextAreaElement | null>(null);
     // Expose DOM ref to parent
     useEffect(() => {
@@ -129,7 +144,7 @@ export const VimTextArea = React.forwardRef<HTMLTextAreaElement, VimTextAreaProp
 
       e.preventDefault();
 
-      // Handle side effects (undo/redo)
+      // Handle side effects (undo/redo/escapeInNormalMode)
       if (result.action === "undo") {
         document.execCommand("undo");
         return;
@@ -138,6 +153,10 @@ export const VimTextArea = React.forwardRef<HTMLTextAreaElement, VimTextAreaProp
         document.execCommand("redo");
         return;
       }
+      if (result.action === "escapeInNormalMode") {
+        onEscapeInNormalMode?.();
+        return;
+      }
 
       // Apply new state to React
       const newState = result.newState;
diff --git a/src/browser/utils/ui/keybinds.ts b/src/browser/utils/ui/keybinds.ts
index 0bc979c542..cbc42d69da 100644
--- a/src/browser/utils/ui/keybinds.ts
+++ b/src/browser/utils/ui/keybinds.ts
@@ -198,7 +198,7 @@ export const KEYBINDS = {
   CANCEL: { key: "Escape" },
 
   /** Cancel editing message (exit edit mode) */
-  CANCEL_EDIT: { key: "q", ctrl: true, macCtrlBehavior: "control" },
+  CANCEL_EDIT: { key: "Escape" },
 
   /** Interrupt active stream (destructive - stops AI generation) */
   // Vim mode: Ctrl+C (familiar from terminal interrupt)
diff --git a/src/browser/utils/vim.ts b/src/browser/utils/vim.ts
index d0e9abd137..411b9408dc 100644
--- a/src/browser/utils/vim.ts
+++ b/src/browser/utils/vim.ts
@@ -19,7 +19,7 @@ export interface VimState {
   pendingOp: null | { op: "d" | "y" | "c"; at: number; args?: string[] };
 }
 
-export type VimAction = "undo" | "redo";
+export type VimAction = "undo" | "redo" | "escapeInNormalMode";
 
 export type VimKeyResult =
   | { handled: false } // Browser should handle this key
@@ -457,9 +457,9 @@ function handleNormalModeKey(state: VimState, key: string, modifiers: KeyModifie
   const opResult = tryHandleOperator(state, key, now);
   if (opResult) return opResult;
 
-  // Stay in normal mode for ESC
+  // Escape in normal mode - signal to parent (e.g., to cancel edit mode)
   if (key === "Escape" || (key === "[" && modifiers.ctrl)) {
-    return { handled: true, newState: state };
+    return { handled: true, newState: state, action: "escapeInNormalMode" };
   }
 
   // Swallow all other single-character keys in normal mode (don't type letters)