diff --git a/apps/web/src/components/ChatView.tsx b/apps/web/src/components/ChatView.tsx
index c296c717066..a74279eefc1 100644
--- a/apps/web/src/components/ChatView.tsx
+++ b/apps/web/src/components/ChatView.tsx
@@ -138,7 +138,7 @@ import { BranchToolbar } from "./BranchToolbar";
 import { resolveShortcutCommand, shortcutLabelForCommand } from "../keybindings";
 import PlanSidebar from "./PlanSidebar";
 import ThreadTerminalDrawer from "./ThreadTerminalDrawer";
-import { ChevronDownIcon, TriangleAlertIcon, WifiOffIcon } from "lucide-react";
+import { ChevronDownIcon, ImageUpIcon, TriangleAlertIcon, WifiOffIcon } from "lucide-react";
 import { cn, randomHex } from "~/lib/utils";
 import { COLLAPSED_SIDEBAR_TITLEBAR_INSET_CLASS } from "~/workspaceTitlebar";
 import { stackedThreadToast, toastManager } from "./ui/toast";
@@ -1196,6 +1196,22 @@ function ChatViewContent(props: ChatViewProps) {
   const localComposerRef = useRef<ChatComposerHandle | null>(null);
   const composerRef = useComposerHandleContext() ?? localComposerRef;
   const [showScrollToBottom, setShowScrollToBottom] = useState(false);
+  const [isDraggingFilesOverView, setIsDraggingFilesOverView] = useState(false);
+  const viewDragDepthRef = useRef(0);
+  const resetViewDragState = useCallback(() => {
+    viewDragDepthRef.current = 0;
+    setIsDraggingFilesOverView(false);
+  }, []);
+
+  // A cancelled drag (Escape) can end without a dragleave on the hovered
+  // target, which would leave the drop overlay stuck. dragend always fires
+  // on the in-page drag source and bubbles to window, so it is the reset of
+  // last resort while the overlay is up.
+  useEffect(() => {
+    if (!isDraggingFilesOverView) return;
+    window.addEventListener("dragend", resetViewDragState);
+    return () => window.removeEventListener("dragend", resetViewDragState);
+  }, [isDraggingFilesOverView, resetViewDragState]);
   const [expandedImage, setExpandedImage] = useState<ExpandedImagePreview | null>(null);
   const [optimisticUserMessages, setOptimisticUserMessages] = useState<ChatMessage[]>([]);
   const optimisticUserMessagesRef = useRef(optimisticUserMessages);
@@ -5084,6 +5100,17 @@ function ChatViewContent(props: ChatViewProps) {
     void onRevertToTurnCountRef.current(targetTurnCount);
   }, []);
 
+  const canDropImagesOnView =
+    activeEnvironmentUnavailableState === null && !(isLocalDraftThread && activeProject === null);
+
+  // If attaching becomes unavailable mid-drag, retract the overlay so it
+  // does not keep inviting a drop that would be discarded.
+  useEffect(() => {
+    if (!canDropImagesOnView) {
+      resetViewDragState();
+    }
+  }, [canDropImagesOnView, resetViewDragState]);
+
   // Empty state: no active thread
   if (!activeThread) {
     return <NoActiveThreadState />;
@@ -5187,8 +5214,57 @@ function ChatViewContent(props: ChatViewProps) {
     ) : null
   ) : null;
 
+  const onViewDragEnter = (event: React.DragEvent<HTMLDivElement>) => {
+    if (!canDropImagesOnView || !event.dataTransfer.types.includes("Files")) return;
+    event.preventDefault();
+    viewDragDepthRef.current += 1;
+    setIsDraggingFilesOverView(true);
+  };
+
+  const onViewDragOver = (event: React.DragEvent<HTMLDivElement>) => {
+    if (!canDropImagesOnView || !event.dataTransfer.types.includes("Files")) return;
+    event.preventDefault();
+    event.dataTransfer.dropEffect = "copy";
+    setIsDraggingFilesOverView(true);
+  };
+
+  // dragenter/dragleave bubble in balanced pairs from descendants, so a
+  // plain depth counter tracks whether the pointer is still inside the
+  // view without inspecting relatedTarget (which nested targets and some
+  // browsers report as null).
+  const onViewDragLeave = (event: React.DragEvent<HTMLDivElement>) => {
+    if (!event.dataTransfer.types.includes("Files")) return;
+    event.preventDefault();
+    viewDragDepthRef.current = Math.max(0, viewDragDepthRef.current - 1);
+    if (viewDragDepthRef.current === 0) {
+      setIsDraggingFilesOverView(false);
+    }
+  };
+
+  const onViewDrop = (event: React.DragEvent<HTMLDivElement>) => {
+    if (!event.dataTransfer.types.includes("Files")) return;
+    event.preventDefault();
+    resetViewDragState();
+    if (!canDropImagesOnView) return;
+    composerRef.current?.addImages(Array.from(event.dataTransfer.files));
+  };
+
   return (
-    <div className="relative flex min-h-0 min-w-0 flex-1 overflow-hidden bg-background">
+    <div
+      className="relative flex min-h-0 min-w-0 flex-1 overflow-hidden bg-background"
+      onDragEnter={onViewDragEnter}
+      onDragOver={onViewDragOver}
+      onDragLeave={onViewDragLeave}
+      onDrop={onViewDrop}
+    >
+      {isDraggingFilesOverView ? (
+        <div className="pointer-events-none absolute inset-0 z-50 flex items-center justify-center bg-background/70 p-6 backdrop-blur-sm">
+          <div className="flex items-center gap-2.5 rounded-2xl border-2 border-dashed border-primary/60 bg-card/90 px-6 py-4 font-medium text-foreground text-sm shadow-lg">
+            <ImageUpIcon className="size-5 text-primary" />
+            Drop images to attach
+          </div>
+        </div>
+      ) : null}
       {rightPanelOpen && !shouldUsePlanSidebarSheet ? panelLayoutControls : null}
       <div
         className={cn(
diff --git a/apps/web/src/components/chat/ChatComposer.tsx b/apps/web/src/components/chat/ChatComposer.tsx
index f3346b4100a..8fcc1b8f51f 100644
--- a/apps/web/src/components/chat/ChatComposer.tsx
+++ b/apps/web/src/components/chat/ChatComposer.tsx
@@ -107,6 +107,7 @@ import {
   LockIcon,
   LockOpenIcon,
   PenLineIcon,
+  PlusIcon,
   XIcon,
 } from "lucide-react";
 import { proposedPlanTitle } from "../../proposedPlan";
@@ -422,6 +423,8 @@ export interface ChatComposerHandle {
   }) => void;
   /** Insert a terminal context from the terminal drawer. */
   addTerminalContext: (selection: TerminalContextSelection) => void;
+  /** Attach image files (e.g. from a view-level drop zone). */
+  addImages: (files: File[]) => void;
   /** Get the current prompt/effort/model state for use in send. */
   getSendContext: () => {
     prompt: string;
@@ -919,6 +922,7 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
   const mobileComposerExpandReleaseFrameRef = useRef<number | null>(null);
   const mobileComposerExpandInFlightRef = useRef(false);
   const dragDepthRef = useRef(0);
+  const attachFileInputRef = useRef<HTMLInputElement | null>(null);
 
   // ------------------------------------------------------------------
   // Derived: composer send state
@@ -1836,8 +1840,20 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
     removeComposerImageFromDraft(imageId);
   };
 
+  const openAttachFilePicker = () => {
+    attachFileInputRef.current?.click();
+  };
+
+  const onAttachFileInputChange = (event: React.ChangeEvent<HTMLInputElement>) => {
+    const files = Array.from(event.target.files ?? []);
+    event.target.value = "";
+    if (files.length === 0) return;
+    addComposerImages(files);
+    focusComposer();
+  };
+
   // ------------------------------------------------------------------
-  // Callbacks: paste / drag
+  // Callbacks: paste
   // ------------------------------------------------------------------
   const onComposerPaste = (event: React.ClipboardEvent<HTMLElement>) => {
     const files = Array.from(event.clipboardData.files);
@@ -1848,41 +1864,6 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
     addComposerImages(imageFiles);
   };
 
-  const onComposerDragEnter = (event: React.DragEvent<HTMLDivElement>) => {
-    if (!event.dataTransfer.types.includes("Files")) return;
-    event.preventDefault();
-    dragDepthRef.current += 1;
-    setIsDragOverComposer(true);
-  };
-
-  const onComposerDragOver = (event: React.DragEvent<HTMLDivElement>) => {
-    if (!event.dataTransfer.types.includes("Files")) return;
-    event.preventDefault();
-    event.dataTransfer.dropEffect = "copy";
-    setIsDragOverComposer(true);
-  };
-
-  const onComposerDragLeave = (event: React.DragEvent<HTMLDivElement>) => {
-    if (!event.dataTransfer.types.includes("Files")) return;
-    event.preventDefault();
-    const nextTarget = event.relatedTarget;
-    if (nextTarget instanceof Node && event.currentTarget.contains(nextTarget)) return;
-    dragDepthRef.current = Math.max(0, dragDepthRef.current - 1);
-    if (dragDepthRef.current === 0) {
-      setIsDragOverComposer(false);
-    }
-  };
-
-  const onComposerDrop = (event: React.DragEvent<HTMLDivElement>) => {
-    if (!event.dataTransfer.types.includes("Files")) return;
-    event.preventDefault();
-    dragDepthRef.current = 0;
-    setIsDragOverComposer(false);
-    const files = Array.from(event.dataTransfer.files);
-    addComposerImages(files);
-    focusComposer();
-  };
-
   const insertComposerTextAtEnd = (
     text: string,
     options?: { ensureLeadingBoundary?: boolean },
@@ -1943,6 +1924,7 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
     window.addEventListener("dragend", onWindowDragEnd);
     return () => window.removeEventListener("dragend", onWindowDragEnd);
   }, [isDragOverComposer]);
+
   const handleInterruptPrimaryAction = useCallback(() => {
     void onInterrupt();
   }, [onInterrupt]);
@@ -2035,6 +2017,15 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
             : null,
         );
       },
+      addImages: (files: File[]) => {
+        if (environmentUnavailable !== null || projectSelectionRequired) return;
+        addComposerImages(files);
+        if (isComposerCollapsedMobile) {
+          expandMobileComposer();
+        } else {
+          focusComposer();
+        }
+      },
       addTerminalContext: (selection: TerminalContextSelection) => {
         if (!activeThread) return;
         const snapshot = composerEditorRef.current?.readSnapshot() ?? {
@@ -2104,6 +2095,8 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
       environmentUnavailable,
       activePendingProgress,
       applyPromptReplacement,
+      isComposerCollapsedMobile,
+      expandMobileComposer,
       isComposerModelPickerOpen,
       readComposerSnapshot,
       selectedModel,
@@ -2129,10 +2122,6 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
           "group rounded-[22px] p-px transition-colors duration-200",
           composerProviderState.composerFrameClassName,
         )}
-        onDragEnter={onComposerDragEnter}
-        onDragOver={onComposerDragOver}
-        onDragLeave={onComposerDragLeave}
-        onDrop={onComposerDrop}
         onDragEnterCapture={composerMentionDragHandlers.onDragEnter}
         onDragOverCapture={composerMentionDragHandlers.onDragOver}
         onDragLeaveCapture={onComposerMentionDragLeaveCapture}
@@ -2558,6 +2547,32 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
               )}
             >
               <div className="-m-1 flex min-w-0 flex-1 items-center gap-1 overflow-x-auto p-1 [scrollbar-width:none] [&::-webkit-scrollbar]:hidden">
+                <input
+                  ref={attachFileInputRef}
+                  type="file"
+                  accept="image/*"
+                  multiple
+                  className="hidden"
+                  onChange={onAttachFileInputChange}
+                />
+                <Tooltip>
+                  <TooltipTrigger
+                    render={
+                      <Button
+                        variant="ghost"
+                        size="icon-sm"
+                        type="button"
+                        className="shrink-0 text-muted-foreground/70 hover:text-foreground/80"
+                        disabled={environmentUnavailable !== null || projectSelectionRequired}
+                        onClick={openAttachFilePicker}
+                        aria-label="Attach images"
+                      />
+                    }
+                  >
+                    <PlusIcon />
+                  </TooltipTrigger>
+                  <TooltipPopup side="top">Attach images</TooltipPopup>
+                </Tooltip>
                 <ProviderModelPicker
                   compact={isComposerFooterCompact}
                   activeInstanceId={selectedInstanceId}