diff --git a/src/gateway/chat-attachments.test.ts b/src/gateway/chat-attachments.test.ts
index d84eb4e63d29..ac5d364a4a56 100644
--- a/src/gateway/chat-attachments.test.ts
+++ b/src/gateway/chat-attachments.test.ts
@@ -32,6 +32,7 @@ import {
   parseMessageWithAttachments,
   persistInboundImagesForTranscript,
   resolveChatAttachmentMaxBytes,
+  stripImageMediaMarkers,
   UnsupportedAttachmentError,
 } from "./chat-attachments.js";
 
@@ -233,7 +234,7 @@ describe("parseMessageWithAttachments", () => {
     expect(ref.label).toBe("report.pdf");
     expect(ref.mediaRef).toMatch(/^media:\/\/inbound\//);
     expect(parsed.message).toBe(`read this\n[media attached: ${ref.mediaRef}]`);
-    expect(parsed.messageWithoutOffloadedImageRefs).toBe(parsed.message);
+    expect(stripImageMediaMarkers(parsed.message, parsed.offloadedRefs)).toBe(parsed.message);
     expect(saveMediaBufferMock).toHaveBeenCalledOnce();
     expect(savedMime()).toBe("application/pdf");
     expect(logs).toHaveLength(0);
@@ -252,7 +253,7 @@ describe("parseMessageWithAttachments", () => {
     expect(parsed.message).toBe(
       `take a look\n[media attached: ${parsed.offloadedRefs[0]?.mediaRef}]`,
     );
-    expect(parsed.messageWithoutOffloadedImageRefs).toBe(parsed.message);
+    expect(stripImageMediaMarkers(parsed.message, parsed.offloadedRefs)).toBe(parsed.message);
     expect(logs).toHaveLength(0);
   });
 
@@ -298,7 +299,9 @@ describe("parseMessageWithAttachments", () => {
     expect(parsed.message).toBe(
       `x\n[media attached: ${pdfRef.mediaRef}]\n[media attached: ${imageRef.mediaRef}]`,
     );
-    expect(parsed.messageWithoutOffloadedImageRefs).toBe(`x\n[media attached: ${pdfRef.mediaRef}]`);
+    expect(stripImageMediaMarkers(parsed.message, parsed.offloadedRefs)).toBe(
+      `x\n[media attached: ${pdfRef.mediaRef}]`,
+    );
     const trailingMediaLines = parsed.message
       .split("\n")
       .filter((line) => line.trim().startsWith("[media attached: media://inbound/"));
@@ -445,7 +448,7 @@ describe("parseMessageWithAttachments validation errors", () => {
   it("passes through unchanged on text-only session with no attachments", async () => {
     const { parsed } = await parseWithWarnings("hello", [], { supportsInlineImages: false });
     expect(parsed.message).toBe("hello");
-    expect(parsed.messageWithoutOffloadedImageRefs).toBe("hello");
+    expect(stripImageMediaMarkers(parsed.message, parsed.offloadedRefs)).toBe("hello");
     expect(parsed.images).toHaveLength(0);
     expect(parsed.offloadedRefs).toHaveLength(0);
     expect(saveMediaBufferMock).not.toHaveBeenCalled();
@@ -474,7 +477,7 @@ describe("parseMessageWithAttachments validation errors", () => {
       expect(parsed.message).toBe(
         `read this\n[media attached: ${parsed.offloadedRefs[0]?.mediaRef}]`,
       );
-      expect(parsed.messageWithoutOffloadedImageRefs).toBe(parsed.message);
+      expect(stripImageMediaMarkers(parsed.message, parsed.offloadedRefs)).toBe(parsed.message);
     } finally {
       await cleanupOffloadedRefs(parsed.offloadedRefs);
     }
@@ -501,7 +504,7 @@ describe("parseMessageWithAttachments validation errors", () => {
       const offloaded = expectDefined(parsed.offloadedRefs[0], "offloaded image ref");
       expect(offloaded.mimeType).toBe("image/png");
       expect(parsed.message).toBe(`see this\n[media attached: ${offloaded.mediaRef}]`);
-      expect(parsed.messageWithoutOffloadedImageRefs).toBe("see this");
+      expect(stripImageMediaMarkers(parsed.message, parsed.offloadedRefs)).toBe("see this");
       expect(parsed.media).toEqual([
         {
           path: offloaded.path,
@@ -537,7 +540,7 @@ describe("parseMessageWithAttachments validation errors", () => {
       expect(parsed.message).toContain(
         "[image attachment omitted: text-only attachment limit reached]",
       );
-      expect(parsed.messageWithoutOffloadedImageRefs).toBe(
+      expect(stripImageMediaMarkers(parsed.message, parsed.offloadedRefs)).toBe(
         "see these\n[image attachment omitted: text-only attachment limit reached]",
       );
       expect(logs).toEqual([
diff --git a/src/gateway/chat-attachments.ts b/src/gateway/chat-attachments.ts
index f48ba05860b6..fc9955aff130 100644
--- a/src/gateway/chat-attachments.ts
+++ b/src/gateway/chat-attachments.ts
@@ -36,7 +36,6 @@ export type OffloadedRef = {
 
 type ParsedMessageWithImages = {
   message: string;
-  messageWithoutOffloadedImageRefs: string;
   images: ChatImageContent[];
   imageOrder: PromptImageOrderEntry[];
   media: MediaFact[];
@@ -64,6 +63,16 @@ const TEXT_ONLY_OFFLOAD_LIMIT = 10;
 
 const DEFAULT_CHAT_ATTACHMENT_MAX_MB = 20;
 
+export function stripImageMediaMarkers(message: string, refs: readonly OffloadedRef[]): string {
+  return refs.reduce((projected, ref) => {
+    const marker = ref.mimeType.startsWith("image/") ? `\n[media attached: ${ref.mediaRef}]` : "";
+    const index = marker ? projected.lastIndexOf(marker) : -1;
+    return index < 0
+      ? projected
+      : projected.slice(0, index) + projected.slice(index + marker.length);
+  }, message);
+}
+
 export async function persistInboundImagesForTranscript(params: {
   images: ChatImageContent[];
   imageOrder: PromptImageOrderEntry[];
@@ -325,7 +334,6 @@ export async function parseMessageWithAttachments(
   if (!attachments || attachments.length === 0) {
     return {
       message,
-      messageWithoutOffloadedImageRefs: message,
       images: [],
       imageOrder: [],
       media: [],
@@ -337,7 +345,6 @@ export async function parseMessageWithAttachments(
   const imageOrder: PromptImageOrderEntry[] = [];
   const offloadedRefs: OffloadedRef[] = [];
   let updatedMessage = message;
-  let messageWithoutOffloadedImageRefs = message;
   let textOnlyImageOffloadCount = 0;
   const savedMediaIds: string[] = [];
 
@@ -431,8 +438,6 @@ export async function parseMessageWithAttachments(
             `${TEXT_ONLY_OFFLOAD_LIMIT} was reached`,
         );
         updatedMessage += "\n[image attachment omitted: text-only attachment limit reached]";
-        messageWithoutOffloadedImageRefs +=
-          "\n[image attachment omitted: text-only attachment limit reached]";
         continue;
       }
 
@@ -469,11 +474,7 @@ export async function parseMessageWithAttachments(
       savedMediaIds.push(savedMedia.id);
 
       const mediaRef = `media://inbound/${savedMedia.id}`;
-      const mediaLine = `\n[media attached: ${mediaRef}]`;
-      updatedMessage += mediaLine;
-      if (!isImage) {
-        messageWithoutOffloadedImageRefs += mediaLine;
-      }
+      updatedMessage += `\n[media attached: ${mediaRef}]`;
       log?.info?.(
         shouldForceImageOffload && isImage
           ? `[Gateway] Offloaded image for text-only model. Saved: ${mediaRef}`
@@ -504,10 +505,6 @@ export async function parseMessageWithAttachments(
 
   return {
     message: updatedMessage !== message ? updatedMessage.trimEnd() : message,
-    messageWithoutOffloadedImageRefs:
-      messageWithoutOffloadedImageRefs !== message
-        ? messageWithoutOffloadedImageRefs.trimEnd()
-        : message,
     images,
     imageOrder,
     media: offloadedRefs.map((ref) => ({
diff --git a/src/gateway/server-methods/chat-send-attachments.ts b/src/gateway/server-methods/chat-send-attachments.ts
index fbf781feb925..e2101f1bea47 100644
--- a/src/gateway/server-methods/chat-send-attachments.ts
+++ b/src/gateway/server-methods/chat-send-attachments.ts
@@ -19,6 +19,7 @@ import {
   type OffloadedRef,
   parseMessageWithAttachments,
   resolveChatAttachmentMaxBytes,
+  stripImageMediaMarkers,
   UnsupportedAttachmentError,
 } from "../chat-attachments.js";
 import { resolveGatewayModelSupportsImages } from "../session-utils.js";
@@ -239,16 +240,15 @@ export async function prepareChatSendAttachments(params: {
             supportsSessionModelImages ||
             explicitOriginTargetsAcpSession(explicitOrigin) ||
             explicitOriginTargetsPlugin;
-          const routeImageOffloadsAsMediaPaths = !supportsImages;
           const parsed = await parseMessageWithAttachments(inboundMessage, normalizedAttachments, {
             maxBytes: resolveChatAttachmentMaxBytes(cfg),
             log: context.logGateway,
             supportsImages,
             acceptNonImage: true,
           });
-          parsedMessage = routeImageOffloadsAsMediaPaths
-            ? parsed.messageWithoutOffloadedImageRefs
-            : parsed.message;
+          parsedMessage = supportsImages
+            ? parsed.message
+            : stripImageMediaMarkers(parsed.message, parsed.offloadedRefs);
           parsedImages = parsed.images;
           imageOrder = parsed.imageOrder;
           offloadedRefs = parsed.offloadedRefs;
@@ -258,7 +258,7 @@ export async function prepareChatSendAttachments(params: {
             workspaceDir: mediaPathOffloadWorkspaceDir,
           } = await prestageMediaPathOffloads({
             offloadedRefs,
-            includeImageRefs: routeImageOffloadsAsMediaPaths,
+            includeImageRefs: !supportsImages,
             cfg,
             sessionKey,
             agentId,