diff --git a/apps/web/src/components/chat/ChatComposer.tsx b/apps/web/src/components/chat/ChatComposer.tsx
index 8f91f08c7093..a739f70bc5d0 100644
--- a/apps/web/src/components/chat/ChatComposer.tsx
+++ b/apps/web/src/components/chat/ChatComposer.tsx
@@ -205,6 +205,7 @@ import {
 import { useOpenPrLink } from "~/lib/openPullRequestLink";
 import {
   collectInlineContextIds,
+  stripInlineContextReferences,
   type ComposerContextReference,
   ensureInlineContextReferences,
   formatInlineContextReference,
@@ -5234,6 +5235,7 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
     options?: {
       readonly source?: ChatFileAttachment["source"];
       readonly selection?: { start: number; end: number };
+      readonly skipImageInlineChip?: boolean;
     },
   ): Promise<boolean> => {
     if (!activeThreadId || files.length === 0 || isRevertingCheckpointRef.current) return false;
@@ -5253,6 +5255,20 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
     // large image is being compressed, and the attachments and errors belong
     // to the thread the paste happened in.
     const threadId = activeThreadId;
+    // Images landing with no prose live on the shelf with no chip. Read before
+    // the awaits below: compression is async and the prompt may change while it
+    // runs. An explicit selection replace and states where the editor refuses
+    // input (connecting, approval, pending questions, project selection) still
+    // get chips so the image is never invisible, unless paste-as-text explicitly
+    // requests no inline image chip.
+    const imageAttachmentsGetChips =
+      !options?.skipImageInlineChip &&
+      (options?.selection !== undefined ||
+        isConnecting ||
+        isComposerApprovalState ||
+        pendingUserInputs.length > 0 ||
+        projectSelectionRequired ||
+        stripInlineContextReferences(promptRef.current).trim().length > 0);
 
     // Validation happens synchronously so concurrent pastes see each other:
     // accepted files reserve their attachment slots (via the pending counter)
@@ -5409,7 +5425,7 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
             : [],
       );
       const storedImages = nextImages.filter((image) => storedImageIds.has(image.id));
-      if (storedImages.length > 0) {
+      if (storedImages.length > 0 && imageAttachmentsGetChips) {
         insertedAny =
           insertAttachmentReferences(storedImages.map(imageContextReference)) || insertedAny;
       }
@@ -5437,6 +5453,8 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
   /**
    * Chips for freshly attached files land at the caret; when the editor cannot take
    * input (approval, pending questions) they are appended so the file is never invisible.
+   * Images skip this when they land with no prose and the editor takes input:
+   * the shelf thumbnail is enough.
    */
   const insertAttachmentReferences = (
     references: ReadonlyArray<ComposerContextReference>,
@@ -5575,7 +5593,7 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
     ) {
       event.preventDefault();
       event.stopPropagation();
-      void addComposerAttachments(files);
+      void addComposerAttachments(files, { skipImageInlineChip: bypassAutoAttachment });
       return;
     }