diff --git a/pkg/tools/mcp/mcp.go b/pkg/tools/mcp/mcp.go
index 48cf1f956..46ea4b77e 100644
--- a/pkg/tools/mcp/mcp.go
+++ b/pkg/tools/mcp/mcp.go
@@ -292,6 +292,13 @@ func (ts *Toolset) watchConnection(ctx context.Context) {
 		if !ts.tryRestart(ctx) {
 			return
 		}
+
+		// After a successful restart, eagerly refresh the tool and prompt
+		// caches and notify the runtime so it picks up the new server's
+		// state. The new server may expose a different set of tools/prompts,
+		// and without this the runtime would keep using its stale copy.
+		ts.refreshToolCache(ctx)
+		ts.refreshPromptCache(ctx)
 	}
 }
 
diff --git a/pkg/tools/mcp/reconnect_test.go b/pkg/tools/mcp/reconnect_test.go
index a95ff4a9c..eeacc52a6 100644
--- a/pkg/tools/mcp/reconnect_test.go
+++ b/pkg/tools/mcp/reconnect_test.go
@@ -17,6 +17,46 @@ import (
 	"github.com/docker/docker-agent/pkg/tools"
 )
 
+// startMCPServer creates a minimal MCP server on addr with the given tools
+// and returns a function to shut it down.
+func startMCPServer(t *testing.T, addr string, mcpTools ...*gomcp.Tool) (shutdown func()) {
+	t.Helper()
+
+	s := gomcp.NewServer(&gomcp.Implementation{Name: "test-server", Version: "1.0.0"}, nil)
+	for _, tool := range mcpTools {
+		s.AddTool(tool, func(_ context.Context, _ *gomcp.CallToolRequest) (*gomcp.CallToolResult, error) {
+			return &gomcp.CallToolResult{
+				Content: []gomcp.Content{&gomcp.TextContent{Text: "ok-" + tool.Name}},
+			}, nil
+		})
+	}
+
+	// Retry Listen until the port is available (e.g. after a server shutdown).
+	var srvLn net.Listener
+	require.Eventually(t, func() bool {
+		var listenErr error
+		srvLn, listenErr = net.Listen("tcp", addr)
+		return listenErr == nil
+	}, 2*time.Second, 50*time.Millisecond, "port %s not available in time", addr)
+
+	srv := &http.Server{
+		Handler: gomcp.NewStreamableHTTPHandler(func(*http.Request) *gomcp.Server { return s }, nil),
+	}
+	go func() { _ = srv.Serve(srvLn) }()
+
+	return func() { _ = srv.Close() }
+}
+
+// allocateAddr returns a free TCP address on localhost.
+func allocateAddr(t *testing.T) string {
+	t.Helper()
+	ln, err := net.Listen("tcp", "127.0.0.1:0")
+	require.NoError(t, err)
+	addr := ln.Addr().String()
+	ln.Close()
+	return addr
+}
+
 // TestRemoteReconnectAfterServerRestart verifies that a Toolset backed by a
 // real remote (streamable-HTTP) MCP server transparently recovers when the
 // server is restarted.
@@ -33,11 +73,7 @@ import (
 func TestRemoteReconnectAfterServerRestart(t *testing.T) {
 	t.Parallel()
 
-	// Use a fixed listener address so we can restart on the same port.
-	ln, err := net.Listen("tcp", "127.0.0.1:0")
-	require.NoError(t, err)
-	addr := ln.Addr().String()
-	ln.Close() // We only needed the address; close so startServer can bind it.
+	addr := allocateAddr(t)
 
 	var callCount atomic.Int32
 
@@ -123,3 +159,82 @@ func TestRemoteReconnectAfterServerRestart(t *testing.T) {
 		t.Fatal("reconnect did not complete: restarted channel was not closed")
 	}
 }
+
+// TestRemoteReconnectRefreshesTools verifies that after a remote MCP server
+// restarts with a different set of tools, the Toolset picks up the new tools
+// and notifies the runtime via the toolsChangedHandler.
+//
+// This is the scenario from https://github.com/docker/docker-agent/issues/2244:
+//   - Server v1 exposes tools [alpha, shared].
+//   - Client connects and caches [alpha, shared].
+//   - Server v1 shuts down; server v2 starts with tools [beta, shared].
+//   - A tool call to "shared" triggers reconnection.
+//   - After reconnection, Tools() must return [beta, shared], not the stale [alpha, shared].
+//   - The toolsChangedHandler must be called so the runtime refreshes its own state.
+func TestRemoteReconnectRefreshesTools(t *testing.T) {
+	t.Parallel()
+
+	addr := allocateAddr(t)
+
+	// "shared" exists on both servers so we can call it to trigger reconnect.
+	sharedTool := &gomcp.Tool{Name: "shared", InputSchema: &jsonschema.Schema{Type: "object"}}
+	alphaTool := &gomcp.Tool{Name: "alpha", InputSchema: &jsonschema.Schema{Type: "object"}}
+	betaTool := &gomcp.Tool{Name: "beta", InputSchema: &jsonschema.Schema{Type: "object"}}
+
+	// --- Start server v1 with tools "alpha" + "shared" ---
+	shutdown1 := startMCPServer(t, addr, alphaTool, sharedTool)
+
+	ts := NewRemoteToolset("ns", fmt.Sprintf("http://%s/mcp", addr), "streamable-http", nil)
+
+	// Track toolsChangedHandler invocations.
+	toolsChangedCh := make(chan struct{}, 1)
+	ts.SetToolsChangedHandler(func() {
+		select {
+		case toolsChangedCh <- struct{}{}:
+		default:
+		}
+	})
+
+	require.NoError(t, ts.Start(t.Context()))
+
+	// Verify initial tools.
+	toolList, err := ts.Tools(t.Context())
+	require.NoError(t, err)
+	require.Len(t, toolList, 2)
+	toolNames := []string{toolList[0].Name, toolList[1].Name}
+	assert.Contains(t, toolNames, "ns_alpha")
+	assert.Contains(t, toolNames, "ns_shared")
+
+	// --- Shut down server v1, start server v2 with tools "beta" + "shared" ---
+	shutdown1()
+
+	shutdown2 := startMCPServer(t, addr, betaTool, sharedTool)
+	t.Cleanup(func() {
+		_ = ts.Stop(t.Context())
+		shutdown2()
+	})
+
+	// Call "shared" to trigger ErrSessionMissing → reconnect.
+	result, callErr := ts.callTool(t.Context(), tools.ToolCall{
+		Function: tools.FunctionCall{Name: "shared", Arguments: "{}"},
+	})
+	require.NoError(t, callErr)
+	assert.Equal(t, "ok-shared", result.Output)
+
+	// Wait for the toolsChangedHandler to be called (signals reconnect + refresh).
+	select {
+	case <-toolsChangedCh:
+		// Good — the handler was called.
+	case <-time.After(30 * time.Second):
+		t.Fatal("timed out waiting for toolsChangedHandler after reconnect")
+	}
+
+	// Verify the toolset now reports the new server's tools.
+	toolList, err = ts.Tools(t.Context())
+	require.NoError(t, err)
+	require.Len(t, toolList, 2, "expected exactly two tools from the new server")
+	toolNames = []string{toolList[0].Name, toolList[1].Name}
+	assert.Contains(t, toolNames, "ns_beta", "expected the new server's tool, got stale tool")
+	assert.Contains(t, toolNames, "ns_shared")
+	assert.NotContains(t, toolNames, "ns_alpha", "stale tool from old server should not be present")
+}