diff --git a/internal/session/query.go b/internal/session/query.go
index ff21d4a83f..88c4cec57a 100644
--- a/internal/session/query.go
+++ b/internal/session/query.go
@@ -292,16 +292,18 @@ where
 	//
 	// The query returns the set of servers that have had connections closed
 	// along with their last update time and the number of connections closed on
-	// each.  If we do not know the last update time, we use the current time.
+	// each. If the worker has not yet sent a session info update, we use the
+	// worker's last update time as the last update time.
 	closeConnectionsForDeadServersCte = `
    with
    dead_workers (worker_id, last_update_time) as (
-         select
-			w.worker_id as worker_id,
-			w.last_request_time as last_update_time
-           from server_worker_session_info_request w
-          where
-			w.last_request_time < wt_sub_seconds_from_now(@grace_period_seconds)
+         select w.public_id as worker_id,
+                coalesce(wsi.last_request_time, w.update_time) as last_update_time
+           from server_worker w
+      left join server_worker_session_info_request wsi on wsi.worker_id = w.public_id 
+          where wsi.last_request_time < wt_sub_seconds_from_now(@grace_period_seconds)
+             or (    wsi.last_request_time is null
+                 and w.update_time < wt_sub_seconds_from_now(@grace_period_seconds))
    ),
    closed_connections (connection_id, worker_id) as (
          update session_connection
diff --git a/internal/tests/cluster/parallel/orphaned_connections_test.go b/internal/tests/cluster/parallel/orphaned_connections_test.go
new file mode 100644
index 0000000000..674416ff07
--- /dev/null
+++ b/internal/tests/cluster/parallel/orphaned_connections_test.go
@@ -0,0 +1,111 @@
+// Copyright (c) HashiCorp, Inc.
+// SPDX-License-Identifier: BUSL-1.1
+
+package parallel
+
+import (
+	"context"
+	"net"
+	"testing"
+	"time"
+
+	"github.com/hashicorp/boundary/api/targets"
+	"github.com/hashicorp/boundary/internal/cmd/config"
+	"github.com/hashicorp/boundary/internal/daemon/controller"
+	"github.com/hashicorp/boundary/internal/daemon/worker"
+	"github.com/hashicorp/boundary/internal/session"
+	"github.com/hashicorp/boundary/internal/tests/helper"
+	"github.com/hashicorp/dawdle"
+	"github.com/hashicorp/go-hclog"
+	"github.com/stretchr/testify/require"
+)
+
+// TestSpeedyOrphanedConnectionCleanup tests that we successfully
+// clean up connections that are orphaned to a worker that never
+// successfully reported a session info.
+func TestSpeedyOrphanedConnectionCleanup(t *testing.T) {
+	t.Parallel()
+	logger := hclog.New(&hclog.LoggerOptions{
+		Name:  t.Name(),
+		Level: hclog.Trace,
+	})
+
+	conf, err := config.DevController()
+	require.NoError(t, err)
+
+	pl, err := net.Listen("tcp", "[::1]:0")
+	require.NoError(t, err)
+	c := controller.NewTestController(t, &controller.TestControllerOpts{
+		Config:                 conf,
+		InitialResourcesSuffix: "1234567890",
+		Logger:                 logger.Named("c1"),
+		PublicClusterAddr:      pl.Addr().String(),
+		WorkerRPCGracePeriod:   2 * time.Second,
+		// Run the scheduler more often to speed up cleanup of orphaned connections
+		SchedulerRunJobInterval: time.Second,
+	})
+
+	helper.ExpectWorkers(t, c)
+
+	// Wire up the testing proxies
+	require.Len(t, c.ClusterAddrs(), 1)
+	proxy, err := dawdle.NewProxy("tcp", "", c.ClusterAddrs()[0],
+		dawdle.WithListener(pl),
+		dawdle.WithRbufSize(256),
+		dawdle.WithWbufSize(256),
+	)
+	require.NoError(t, err)
+	t.Cleanup(func() {
+		_ = proxy.Close()
+	})
+	require.NotEmpty(t, proxy.ListenerAddr())
+
+	w := worker.NewTestWorker(t, &worker.TestWorkerOpts{
+		WorkerAuthKms:    c.Config().WorkerAuthKms,
+		InitialUpstreams: []string{proxy.ListenerAddr()},
+		Logger:           logger.Named("w1"),
+		SuccessfulControllerRPCGracePeriodDuration: 2 * time.Second,
+		WorkerRPCInterval:                          time.Second,
+	})
+
+	helper.ExpectWorkers(t, c, w)
+
+	// Use an independent context for test things that take a context so
+	// that we aren't tied to any timeouts in the controller, etc. This
+	// can interfere with some of the test operations.
+	ctx := context.Background()
+
+	// Connect target
+	client := c.Client()
+	client.SetToken(c.Token().Token)
+	tcl := targets.NewClient(client)
+	tgt, err := tcl.Read(ctx, "ttcp_1234567890")
+	require.NoError(t, err)
+	require.NotNil(t, tgt)
+
+	// Create test server, update default port on target
+	ts := helper.NewTestTcpServer(t)
+	require.NotNil(t, ts)
+	t.Cleanup(ts.Close)
+	tgt, err = tcl.Update(ctx, tgt.Item.Id, tgt.Item.Version, targets.WithTcpTargetDefaultPort(ts.Port()), targets.WithSessionConnectionLimit(-1))
+	require.NoError(t, err)
+	require.NotNil(t, tgt)
+
+	// Authorize and connect
+	sess := helper.NewTestSession(ctx, t, tcl, "ttcp_1234567890")
+	sConn := sess.Connect(ctx, t)
+
+	// Run initial send/receive test, make sure things are working
+	t.Log("running initial send/recv test")
+	sConn.TestSendRecvAll(t)
+
+	// Kill the link before the worker has a chance to send a session info
+	t.Log("pausing controller/worker link")
+	proxy.Pause()
+	t.Cleanup(proxy.Resume) // Resume the proxy on cleanup to allow other cleanup to run
+
+	// Both the worker and the controller should detect that the worker is dead
+	// and close the connection.
+	sess.ExpectConnectionStateOnWorker(ctx, t, w, session.StatusClosed)
+	sess.ExpectConnectionStateOnController(ctx, t, c.Controller().ConnectionRepoFn, session.StatusClosed)
+}