diff --git a/docs/thinking.md b/docs/thinking.md
index 355a97ab3..c95fb765f 100644
--- a/docs/thinking.md
+++ b/docs/thinking.md
@@ -32,7 +32,7 @@ read_when:
 - Levels: `on|full` or `off` (default).
 - Directive-only message toggles session verbose and replies `Verbose logging enabled.` / `Verbose logging disabled.`; invalid levels return a hint without changing state.
 - Inline directive affects only that message; session/global defaults apply otherwise.
-- When verbose is on, agents that emit structured tool results (Pi, other JSON agents) send each tool result back as its own metadata-only message, prefixed with `[🛠️ <tool-name> <arg>]` when available (path/command); the tool output itself is not forwarded.
+- When verbose is on, agents that emit structured tool results (Pi, other JSON agents) send each tool result back as its own metadata-only message, prefixed with `[🛠️ <tool-name> <arg>]` when available (path/command); the tool output itself is not forwarded. These tool summaries are sent as soon as each tool finishes (separate bubbles), not as streaming deltas.
 
 ## Heartbeats
 - Heartbeat probe body is `HEARTBEAT`. Inline directives in a heartbeat message apply as usual (but avoid changing session defaults from heartbeats).
diff --git a/src/agents/pi-embedded.ts b/src/agents/pi-embedded.ts
index 46a16f935..5e54cdc8e 100644
--- a/src/agents/pi-embedded.ts
+++ b/src/agents/pi-embedded.ts
@@ -221,6 +221,10 @@ export async function runEmbeddedPiAgent(params: {
     text?: string;
     mediaUrls?: string[];
   }) => void | Promise<void>;
+  onToolResult?: (payload: {
+    text?: string;
+    mediaUrls?: string[];
+  }) => void | Promise<void>;
   onAgentEvent?: (evt: {
     stream: string;
     data: Record<string, unknown>;
@@ -415,6 +419,24 @@ export async function runEmbeddedPiAgent(params: {
                 isError,
               },
             });
+            if (params.verboseLevel === "on" && params.onToolResult) {
+              const agg = formatToolAggregate(
+                toolName,
+                meta ? [meta] : undefined,
+              );
+              const { text: cleanedText, mediaUrls } =
+                splitMediaFromOutput(agg);
+              if (cleanedText || (mediaUrls && mediaUrls.length > 0)) {
+                try {
+                  void params.onToolResult({
+                    text: cleanedText,
+                    mediaUrls: mediaUrls?.length ? mediaUrls : undefined,
+                  });
+                } catch {
+                  // ignore tool result delivery failures
+                }
+              }
+            }
           }
 
           if (evt.type === "message_update") {
@@ -566,6 +588,7 @@ export async function runEmbeddedPiAgent(params: {
       const inlineToolResults =
         params.verboseLevel === "on" &&
         !params.onPartialReply &&
+        !params.onToolResult &&
         toolMetas.length > 0;
       if (inlineToolResults) {
         for (const { toolName, meta } of toolMetas) {
diff --git a/src/auto-reply/reply.ts b/src/auto-reply/reply.ts
index 92789a9e7..56214c6ab 100644
--- a/src/auto-reply/reply.ts
+++ b/src/auto-reply/reply.ts
@@ -760,6 +760,13 @@ export async function getReplyFromConfig(
               mediaUrls: payload.mediaUrls,
             })
         : undefined,
+      onToolResult: opts?.onToolResult
+        ? (payload) =>
+            opts.onToolResult?.({
+              text: payload.text,
+              mediaUrls: payload.mediaUrls,
+            })
+        : undefined,
     });
 
     const payloadArray = runResult.payloads ?? [];
diff --git a/src/auto-reply/types.ts b/src/auto-reply/types.ts
index 38916c685..27ddace0b 100644
--- a/src/auto-reply/types.ts
+++ b/src/auto-reply/types.ts
@@ -2,6 +2,7 @@ export type GetReplyOptions = {
   onReplyStart?: () => Promise<void> | void;
   isHeartbeat?: boolean;
   onPartialReply?: (payload: ReplyPayload) => Promise<void> | void;
+  onToolResult?: (payload: ReplyPayload) => Promise<void> | void;
 };
 
 export type ReplyPayload = {
diff --git a/src/web/auto-reply.ts b/src/web/auto-reply.ts
index 4415ea455..1ded0540f 100644
--- a/src/web/auto-reply.ts
+++ b/src/web/auto-reply.ts
@@ -887,6 +887,55 @@ export async function monitorWebProvider(
         }
       }
 
+      const responsePrefix = cfg.inbound?.responsePrefix;
+      let toolSendChain: Promise<void> = Promise.resolve();
+      const sendToolResult = (payload: ReplyPayload) => {
+        if (
+          !payload?.text &&
+          !payload?.mediaUrl &&
+          !(payload?.mediaUrls?.length ?? 0)
+        ) {
+          return;
+        }
+        const toolPayload: ReplyPayload = { ...payload };
+        if (
+          responsePrefix &&
+          toolPayload.text &&
+          toolPayload.text.trim() !== HEARTBEAT_TOKEN &&
+          !toolPayload.text.startsWith(responsePrefix)
+        ) {
+          toolPayload.text = `${responsePrefix} ${toolPayload.text}`;
+        }
+        toolSendChain = toolSendChain
+          .then(async () => {
+            await deliverWebReply({
+              replyResult: toolPayload,
+              msg,
+              maxMediaBytes,
+              replyLogger,
+              runtime,
+              connectionId,
+              skipLog: true,
+            });
+            if (toolPayload.text) {
+              recentlySent.add(toolPayload.text);
+              if (recentlySent.size > MAX_RECENT_MESSAGES) {
+                const firstKey = recentlySent.values().next().value;
+                if (firstKey) recentlySent.delete(firstKey);
+              }
+            }
+          })
+          .catch((err) => {
+            console.error(
+              danger(
+                `Failed sending web tool update to ${msg.from ?? conversationId}: ${String(
+                  err,
+                )}`,
+              ),
+            );
+          });
+      };
+
       const replyResult = await (replyResolver ?? getReplyFromConfig)(
         {
           Body: combinedBody,
@@ -905,6 +954,7 @@ export async function monitorWebProvider(
         },
         {
           onReplyStart: msg.sendComposing,
+          onToolResult: sendToolResult,
         },
       );
 
@@ -919,8 +969,7 @@ export async function monitorWebProvider(
         return;
       }
 
-      // Apply response prefix if configured (skip for HEARTBEAT_OK to preserve exact match)
-      const responsePrefix = cfg.inbound?.responsePrefix;
+      await toolSendChain;
 
       for (const replyPayload of replyList) {
         if (