diff --git a/web/src/structured.ts b/web/src/structured.ts
index 8c9d7eb..288d8b9 100644
--- a/web/src/structured.ts
+++ b/web/src/structured.ts
@@ -251,6 +251,8 @@ export function createStructuredConnection(
   let activityTimer: number | null = null;
   const promptQueue: QueuedPrompt[] = [];
   let promptRequestPending = false;
+  /** Server path → object URL for uploaded images, so user bubbles can show previews. */
+  const imageObjectUrls = new Map<string, string>();
 
   // Within 64px, wheel and touch imprecision should still count as following.
   const FOLLOW_BOTTOM_THRESHOLD_PX = 64;
@@ -381,6 +383,9 @@ export function createStructuredConnection(
     }
   }
 
+  /** Pattern matching `Attached file "name": "path"` references appended by dispatchPrompt. */
+  const attachedFileRe = /Attached file "(?:[^"\\]|\\.)*": "((?:[^"\\]|\\.)*)"/g;
+
   function buildRowElement(row: TranscriptRow): HTMLElement | null {
     const el = buildTranscriptRow(
       row,
@@ -397,6 +402,39 @@ export function createStructuredConnection(
     if (el.querySelector(".st-tool-head")?.getAttribute("aria-expanded") !== "true") {
       expandedRowIds.delete(row.id);
     }
+    // Inject image previews into user message bubbles and strip the path text.
+    if (row.kind === "user" && imageObjectUrls.size > 0) {
+      const data = row.data as { content?: { type: string; text?: string } } | undefined;
+      const text = data?.content?.type === "text" ? data.content.text ?? "" : "";
+      const body = el.querySelector(".st-body");
+      if (body && text) {
+        const images: string[] = [];
+        attachedFileRe.lastIndex = 0;
+        let match: RegExpExecArray | null;
+        while ((match = attachedFileRe.exec(text)) !== null) {
+          const serverPath = JSON.parse(`"${match[1]}"`);
+          const objectUrl = imageObjectUrls.get(serverPath);
+          if (objectUrl) images.push(objectUrl);
+        }
+        if (images.length > 0) {
+          // Strip attachment reference lines from the displayed text.
+          const userText = body.querySelector(".st-user-text");
+          if (userText) {
+            const cleaned = text.replace(/\n\nAttached file "[^"]*": "[^"]*"/g, "").trim();
+            userText.textContent = cleaned;
+            if (!cleaned) userText.remove();
+          }
+          for (const src of images) {
+            const img = document.createElement("img");
+            img.className = "st-user-image";
+            img.src = src;
+            img.alt = "Uploaded image";
+            img.loading = "lazy";
+            body.appendChild(img);
+          }
+        }
+      }
+    }
     return el;
   }
 
@@ -1002,6 +1040,9 @@ export function createStructuredConnection(
       for (const attachment of submittedAttachments) {
         if (disposed) return;
         if (!attachment.path) attachment.path = (await uploadStructuredFile(sessionId, attachment.file)).path;
+        if (attachment.path && attachment.file.type.startsWith("image/")) {
+          imageObjectUrls.set(attachment.path, URL.createObjectURL(attachment.file));
+        }
       }
       if (disposed) return;
       const references = submittedAttachments.map(({ file, path }) =>
@@ -1241,6 +1282,8 @@ export function createStructuredConnection(
       closeCurrentSocket();
       expandedRowIds.clear();
       expandedGroupIds.clear();
+      for (const url of imageObjectUrls.values()) URL.revokeObjectURL(url);
+      imageObjectUrls.clear();
       scrollEl.removeEventListener("scroll", onTranscriptScroll);
       scrollEl.removeEventListener("click", onTranscriptClick, true);
       scrollEl.removeEventListener("wheel", stopSmoothFollow);
diff --git a/web/src/styles.css b/web/src/styles.css
index 75a6f48..1528074 100644
--- a/web/src/styles.css
+++ b/web/src/styles.css
@@ -2396,6 +2396,15 @@ input.leaf-rename:focus {
   overflow-wrap: anywhere;
 }
 
+.st-user-image {
+  display: block;
+  max-width: min(100%, 480px);
+  max-height: 360px;
+  margin-top: var(--sp-2);
+  border-radius: var(--r-1);
+  object-fit: contain;
+}
+
 /* agent prose: no card, no background — plain text is the point */
 .st-row-agent .st-body p {
   margin: 0 0 var(--sp-2);