diff --git a/CHANGELOG.md b/CHANGELOG.md
index a9794a1e8da..9bea4d7c192 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -19,6 +19,7 @@ Docs: https://docs.openclaw.ai
 ### Fixes
 
 - fix(gateway): enforce allowRequestSessionKey gate on template-rendered mapping sessionKeys. (#69381) Thanks @pgondhi987.
+- Webchat/images: treat inline image attachments as media for empty-turn gating while still ignoring metadata-only blank turns. (#69474) Thanks @Jaswir.
 - OpenAI/Responses: resolve `/think` levels against each GPT model's supported reasoning efforts so `/think off` no longer becomes high reasoning or sends unsupported `reasoning.effort: "none"` payloads.
 - Lobster/TaskFlow: allow managed approval resumes to use `approvalId` without a resume token, and persist that id in approval wait state. (#69559) Thanks @kirkluokun.
 - Plugins/startup: install bundled runtime dependencies into each plugin's own runtime directory, reuse source-checkout repair caches after rebuilds, and log only packages that were actually installed so repeated Gateway starts stay quiet once deps are present.
diff --git a/src/auto-reply/reply/get-reply-run.media-only.test.ts b/src/auto-reply/reply/get-reply-run.media-only.test.ts
index c1bf3873d72..2f3d61865e9 100644
--- a/src/auto-reply/reply/get-reply-run.media-only.test.ts
+++ b/src/auto-reply/reply/get-reply-run.media-only.test.ts
@@ -112,6 +112,7 @@ let runReplyAgent: typeof import("./agent-runner.runtime.js").runReplyAgent;
 let routeReply: typeof import("./route-reply.runtime.js").routeReply;
 let drainFormattedSystemEvents: typeof import("./session-system-events.js").drainFormattedSystemEvents;
 let resolveTypingMode: typeof import("./typing-mode.js").resolveTypingMode;
+let buildInboundUserContextPrefix: typeof import("./inbound-meta.js").buildInboundUserContextPrefix;
 let getActiveReplyRunCount: typeof import("./reply-run-registry.js").getActiveReplyRunCount;
 let replyRunTesting: typeof import("./reply-run-registry.js").__testing;
 let loadScopeCounter = 0;
@@ -221,6 +222,7 @@ describe("runPreparedReply media-only handling", () => {
     ({ routeReply } = await import("./route-reply.runtime.js"));
     ({ drainFormattedSystemEvents } = await import("./session-system-events.js"));
     ({ resolveTypingMode } = await import("./typing-mode.js"));
+    ({ buildInboundUserContextPrefix } = await import("./inbound-meta.js"));
     ({ __testing: replyRunTesting, getActiveReplyRunCount } =
       await import("./reply-run-registry.js"));
   });
@@ -310,6 +312,83 @@ describe("runPreparedReply media-only handling", () => {
     expect(vi.mocked(runReplyAgent)).not.toHaveBeenCalled();
   });
 
+  it("still skips metadata-only turns when inbound context adds chat_id", async () => {
+    vi.mocked(buildInboundUserContextPrefix).mockReturnValueOnce(
+      [
+        "Conversation info (untrusted metadata):",
+        "```json",
+        JSON.stringify({ chat_id: "paperclip:issue:abc" }, null, 2),
+        "```",
+      ].join("\n"),
+    );
+
+    const result = await runPreparedReply(
+      baseParams({
+        ctx: {
+          Body: "",
+          RawBody: "",
+          CommandBody: "",
+        },
+        sessionCtx: {
+          Body: "",
+          BodyStripped: "",
+          Provider: "paperclip",
+          OriginatingChannel: "paperclip",
+          OriginatingTo: "paperclip:issue:abc",
+          ChatType: "direct",
+        },
+      }),
+    );
+
+    expect(result).toEqual({
+      text: "I didn't receive any text in your message. Please resend or add a caption.",
+    });
+    expect(vi.mocked(runReplyAgent)).not.toHaveBeenCalled();
+  });
+
+  it("allows webchat pure-image turns when image content is carried outside MediaPath", async () => {
+    vi.mocked(buildInboundUserContextPrefix).mockReturnValueOnce(
+      [
+        "Conversation info (untrusted metadata):",
+        "```json",
+        JSON.stringify({ provider: "webchat", chat_id: "webchat:local" }, null, 2),
+        "```",
+      ].join("\n"),
+    );
+
+    const result = await runPreparedReply(
+      baseParams({
+        ctx: {
+          Body: "",
+          RawBody: "",
+          CommandBody: "",
+        },
+        sessionCtx: {
+          Body: "",
+          BodyStripped: "",
+          Provider: "webchat",
+          OriginatingChannel: "webchat",
+          OriginatingTo: "webchat:local",
+          ChatType: "direct",
+        },
+        opts: {
+          images: [
+            {
+              type: "input_image",
+              image_url: "data:image/png;base64,AAAA",
+            },
+          ] as never,
+        },
+      }),
+    );
+
+    expect(result).toEqual({ text: "ok" });
+    expect(vi.mocked(runReplyAgent)).toHaveBeenCalledOnce();
+    const call = vi.mocked(runReplyAgent).mock.calls[0]?.[0];
+    expect(call?.followupRun.prompt).toContain("webchat:local");
+    expect(call?.followupRun.prompt).toContain("[User sent media without caption]");
+  });
+
   it("does not send a standalone reset notice for reply-producing /new turns", async () => {
     await runPreparedReply(
       baseParams({
diff --git a/src/auto-reply/reply/get-reply-run.ts b/src/auto-reply/reply/get-reply-run.ts
index 7393adcd844..a58d1a5b988 100644
--- a/src/auto-reply/reply/get-reply-run.ts
+++ b/src/auto-reply/reply/get-reply-run.ts
@@ -42,6 +42,7 @@ import type { InlineDirectives } from "./directive-handling.js";
 import { shouldUseReplyFastTestRuntime } from "./get-reply-fast-path.js";
 import { resolvePreparedReplyQueueState } from "./get-reply-run-queue.js";
 import { buildGroupChatContext, buildGroupIntro } from "./groups.js";
+import { hasInboundMedia } from "./inbound-media.js";
 import { buildInboundMetaSystemPrompt, buildInboundUserContextPrefix } from "./inbound-meta.js";
 import type { createModelSelectionState } from "./model-selection.js";
 import { resolveOriginMessageProvider } from "./origin-routing.js";
@@ -375,11 +376,9 @@ export async function runPreparedReply(
   const baseBodyForPrompt = isBareSessionReset
     ? [startupContextPrelude, baseBodyFinal].filter(Boolean).join("\n\n")
     : [inboundUserContext, baseBodyFinal].filter(Boolean).join("\n\n");
-  const baseBodyTrimmed = baseBodyForPrompt.trim();
-  const hasMediaAttachment = Boolean(
-    sessionCtx.MediaPath || (sessionCtx.MediaPaths && sessionCtx.MediaPaths.length > 0),
-  );
-  if (!baseBodyTrimmed && !hasMediaAttachment) {
+  const hasUserBody = baseBodyFinal.trim().length > 0;
+  const hasMediaAttachment = hasInboundMedia(sessionCtx) || (opts?.images?.length ?? 0) > 0;
+  if (!hasUserBody && !hasMediaAttachment) {
     // Skip onReplyStart when typing is suppressed (e.g. sendPolicy deny) —
     // otherwise channels that wire onReplyStart to typing indicators leak
     // visible signals even though outbound delivery is suppressed.
@@ -394,9 +393,9 @@ export async function runPreparedReply(
   }
   // When the user sends media without text, provide a minimal body so the agent
   // run proceeds and the image/document is injected by the embedded runner.
-  const effectiveBaseBody = baseBodyTrimmed
+  const effectiveBaseBody = hasUserBody
     ? baseBodyForPrompt
-    : "[User sent media without caption]";
+    : [inboundUserContext, "[User sent media without caption]"].filter(Boolean).join("\n\n");
   let prefixedBodyBase = await applySessionHints({
     baseBody: effectiveBaseBody,
     abortedLastRun,