diff --git a/cli/cliutil/sink.go b/cli/cliutil/sink.go
new file mode 100644
index 0000000000000..0943d51c5ed5c
--- /dev/null
+++ b/cli/cliutil/sink.go
@@ -0,0 +1,38 @@
+package cliutil
+
+import (
+	"io"
+	"sync"
+)
+
+type discardAfterClose struct {
+	sync.Mutex
+	wc     io.WriteCloser
+	closed bool
+}
+
+// DiscardAfterClose is an io.WriteCloser that discards writes after it is closed without errors.
+// It is useful as a target for a slog.Sink such that an underlying WriteCloser, like a file, can
+// be cleaned up without race conditions from still-active loggers.
+func DiscardAfterClose(wc io.WriteCloser) io.WriteCloser {
+	return &discardAfterClose{wc: wc}
+}
+
+func (d *discardAfterClose) Write(p []byte) (n int, err error) {
+	d.Lock()
+	defer d.Unlock()
+	if d.closed {
+		return len(p), nil
+	}
+	return d.wc.Write(p)
+}
+
+func (d *discardAfterClose) Close() error {
+	d.Lock()
+	defer d.Unlock()
+	if d.closed {
+		return nil
+	}
+	d.closed = true
+	return d.wc.Close()
+}
diff --git a/cli/cliutil/sink_test.go b/cli/cliutil/sink_test.go
new file mode 100644
index 0000000000000..49b8b5cbe9636
--- /dev/null
+++ b/cli/cliutil/sink_test.go
@@ -0,0 +1,54 @@
+package cliutil_test
+
+import (
+	"errors"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/cli/cliutil"
+)
+
+func TestDiscardAfterClose(t *testing.T) {
+	t.Parallel()
+	exErr := errors.New("test")
+	fwc := &fakeWriteCloser{err: exErr}
+	uut := cliutil.DiscardAfterClose(fwc)
+
+	n, err := uut.Write([]byte("one"))
+	require.Equal(t, 3, n)
+	require.NoError(t, err)
+
+	n, err = uut.Write([]byte("two"))
+	require.Equal(t, 3, n)
+	require.NoError(t, err)
+
+	err = uut.Close()
+	require.Equal(t, exErr, err)
+
+	n, err = uut.Write([]byte("three"))
+	require.Equal(t, 5, n)
+	require.NoError(t, err)
+
+	require.Len(t, fwc.writes, 2)
+	require.EqualValues(t, "one", fwc.writes[0])
+	require.EqualValues(t, "two", fwc.writes[1])
+}
+
+type fakeWriteCloser struct {
+	writes [][]byte
+	closed bool
+	err    error
+}
+
+func (f *fakeWriteCloser) Write(p []byte) (n int, err error) {
+	q := make([]byte, len(p))
+	copy(q, p)
+	f.writes = append(f.writes, q)
+	return len(p), nil
+}
+
+func (f *fakeWriteCloser) Close() error {
+	f.closed = true
+	return f.err
+}
diff --git a/cli/ssh.go b/cli/ssh.go
index fd0474281959a..9287ee1ef13c0 100644
--- a/cli/ssh.go
+++ b/cli/ssh.go
@@ -28,6 +28,7 @@ import (
 
 	"github.com/coder/coder/v2/cli/clibase"
 	"github.com/coder/coder/v2/cli/cliui"
+	"github.com/coder/coder/v2/cli/cliutil"
 	"github.com/coder/coder/v2/coderd/autobuild/notify"
 	"github.com/coder/coder/v2/coderd/util/ptr"
 	"github.com/coder/coder/v2/codersdk"
@@ -114,12 +115,13 @@ func (r *RootCmd) ssh() *clibase.Cmd {
 				if err != nil {
 					return xerrors.Errorf("error opening %s for logging: %w", logDirPath, err)
 				}
+				dc := cliutil.DiscardAfterClose(logFile)
 				go func() {
 					wg.Wait()
-					_ = logFile.Close()
+					_ = dc.Close()
 				}()
 
-				logger = slog.Make(sloghuman.Sink(logFile))
+				logger = logger.AppendSinks(sloghuman.Sink(dc))
 				if r.verbose {
 					logger = logger.Leveled(slog.LevelDebug)
 				}
diff --git a/cli/vscodessh.go b/cli/vscodessh.go
index 6b30b9c3c64ec..87458d85833af 100644
--- a/cli/vscodessh.go
+++ b/cli/vscodessh.go
@@ -21,6 +21,7 @@ import (
 	"cdr.dev/slog/sloggers/sloghuman"
 
 	"github.com/coder/coder/v2/cli/clibase"
+	"github.com/coder/coder/v2/cli/cliutil"
 	"github.com/coder/coder/v2/codersdk"
 )
 
@@ -137,15 +138,16 @@ func (r *RootCmd) vscodeSSH() *clibase.Cmd {
 			// command via the ProxyCommand SSH option.
 			pid := os.Getppid()
 
-			var logger slog.Logger
+			logger := slog.Make()
 			if logDir != "" {
 				logFilePath := filepath.Join(logDir, fmt.Sprintf("%d.log", pid))
 				logFile, err := fs.OpenFile(logFilePath, os.O_CREATE|os.O_WRONLY, 0o600)
 				if err != nil {
 					return xerrors.Errorf("open log file %q: %w", logFilePath, err)
 				}
-				defer logFile.Close()
-				logger = slog.Make(sloghuman.Sink(logFile)).Leveled(slog.LevelDebug)
+				dc := cliutil.DiscardAfterClose(logFile)
+				defer dc.Close()
+				logger = logger.AppendSinks(sloghuman.Sink(dc)).Leveled(slog.LevelDebug)
 			}
 			if r.disableDirect {
 				logger.Info(ctx, "direct connections disabled")