diff --git a/clients/web/src/components/views/InspectorView/InspectorView.test.tsx b/clients/web/src/components/views/InspectorView/InspectorView.test.tsx
index ec979431..99197eaf 100644
--- a/clients/web/src/components/views/InspectorView/InspectorView.test.tsx
+++ b/clients/web/src/components/views/InspectorView/InspectorView.test.tsx
@@ -1343,6 +1343,39 @@ describe("InspectorView", () => {
       ).toBeInTheDocument();
     });
 
+    it("opens the monitoring column when a connection is established", async () => {
+      monitorWide.value = true;
+      const { rerender } = renderWithMantine(
+        <StatefulInspectorViewHost
+          {...makeProps({
+            servers: [httpServer],
+            activeServer: undefined,
+            connectionStatus: "disconnected",
+          })}
+        />,
+      );
+      // Disconnected: the column is closed.
+      expect(
+        screen.queryByRole("button", { name: "Close monitoring column" }),
+      ).toBeNull();
+
+      // Connecting opens it (the disconnected → connected transition).
+      rerender(<StatefulInspectorViewHost {...connectedHttp()} />);
+      expect(
+        await screen.findByRole("button", { name: "Close monitoring column" }),
+      ).toBeInTheDocument();
+    });
+
+    it("does not auto-open on a mount that starts already connected", () => {
+      // No disconnected → connected transition, and no stored preference, so the
+      // column stays closed (a user who closed it isn't fought on remount).
+      monitorWide.value = true;
+      renderWithMantine(<StatefulInspectorViewHost {...connectedHttp()} />);
+      expect(
+        screen.queryByRole("button", { name: "Close monitoring column" }),
+      ).toBeNull();
+    });
+
     it("pins the monitor group into the column and removes it from the header", async () => {
       monitorWide.value = true;
       renderWithMantine(<StatefulInspectorViewHost {...connectedHttp()} />);
diff --git a/clients/web/src/components/views/InspectorView/InspectorView.tsx b/clients/web/src/components/views/InspectorView/InspectorView.tsx
index bd520298..b61f1ed3 100644
--- a/clients/web/src/components/views/InspectorView/InspectorView.tsx
+++ b/clients/web/src/components/views/InspectorView/InspectorView.tsx
@@ -1,4 +1,11 @@
-import { useMemo, useState, type ReactNode, type Ref } from "react";
+import {
+  useEffect,
+  useMemo,
+  useRef,
+  useState,
+  type ReactNode,
+  type Ref,
+} from "react";
 import {
   AppShell,
   Box,
@@ -647,6 +654,23 @@ export function InspectorView({
     getInitialValueInEffect: false,
   });
 
+  // Open the monitoring column when a connection is established (#1616). Gated on
+  // the disconnected → connected *transition* (via the ref) rather than the
+  // "connected" state itself, so it fires on an actual connect — not on every
+  // render while connected, and not on a mount that starts already-connected
+  // (which would fight a user who closed it). The column still only *appears*
+  // when wide + a monitor tab is available (`effectivePinned`); this just sets
+  // the preference. Closing it stays closed until the next connect, since this
+  // effect only re-runs when `connectionStatus` changes.
+  const wasConnectedRef = useRef(connectionStatus === "connected");
+  useEffect(() => {
+    const isConnected = connectionStatus === "connected";
+    if (isConnected && !wasConnectedRef.current) {
+      setMonitorPinned(true);
+    }
+    wasConnectedRef.current = isConnected;
+  }, [connectionStatus, setMonitorPinned]);
+
   const appTools = useMemo<Tool[]>(() => {
     return tools.filter((tool) => {
       try {