diff --git a/lib/kube/proxy/sess.go b/lib/kube/proxy/sess.go
index e2fd43ee8f060..a60753e934420 100644
--- a/lib/kube/proxy/sess.go
+++ b/lib/kube/proxy/sess.go
@@ -445,7 +445,6 @@ func (s *session) launch() error {
 	}()
 
 	s.log.Debugf("Launching session: %v", s.id)
-	s.BroadcastMessage("Connecting to %v over K8S", s.podName)
 
 	q := s.req.URL.Query()
 	request := &remoteCommandRequest{
@@ -463,6 +462,9 @@ func (s *session) launch() error {
 		pingPeriod:         s.forwarder.cfg.ConnPingPeriod,
 	}
 
+	s.podName = request.podName
+	s.BroadcastMessage("Connecting to %v over K8S", s.podName)
+
 	eventPodMeta := request.eventPodMeta(request.context, s.sess.creds)
 	s.io.OnWriteError = func(idString string, err error) {
 		s.mu.Lock()
@@ -541,7 +543,6 @@ func (s *session) launch() error {
 		}
 	}()
 
-	s.podName = request.podName
 	err = s.trackerUpdateState(types.SessionState_SessionStateRunning)
 	if err != nil {
 		s.log.Warn("Failed to set tracker state to running")
diff --git a/lib/srv/termmanager.go b/lib/srv/termmanager.go
index b9bf958ca3c33..33dea82fc944f 100644
--- a/lib/srv/termmanager.go
+++ b/lib/srv/termmanager.go
@@ -23,7 +23,11 @@ import (
 	log "github.com/sirupsen/logrus"
 )
 
-const maxHistory = 1000
+// maxHistoryBytes is the maximum bytes that are retained as history and broadcasted to new clients.
+const maxHistoryBytes = 1000
+
+// maxPausedHistoryBytes is maximum bytes that are buffered when a session is paused.
+const maxPausedHistoryBytes = 10000
 
 // TermManager handles the streams of terminal-like sessions.
 // It performs a number of tasks including:
@@ -70,18 +74,7 @@ func NewTermManager() *TermManager {
 
 func (g *TermManager) writeToClients(p []byte) int {
 	g.lastWasBroadcast = false
-	truncateFront := func(slice []byte, max int) []byte {
-		if len(slice) > max {
-			return slice[len(slice)-max:]
-		}
-
-		return slice
-	}
-
-	g.history = append(g.history, truncateFront(p, maxHistory)...)
-	if len(g.history) > maxHistory {
-		g.history = g.history[:maxHistory]
-	}
+	g.history = truncateFront(append(g.history, p...), maxHistoryBytes)
 
 	atomic.AddUint64(&g.countWritten, uint64(len(p)))
 	for key, w := range g.writers {
@@ -113,7 +106,9 @@ func (g *TermManager) Write(p []byte) (int, error) {
 	if g.on {
 		g.writeToClients(p)
 	} else {
-		g.buffer = append(g.buffer, p...)
+		// Only keep the last maxPausedHistoryBytes of stdout/stderr while the session is paused.
+		// The alternative is flushing to disk but this should be a pretty rare occurrence and shouldn't be an issue in practice.
+		g.buffer = truncateFront(append(g.buffer, p...), maxPausedHistoryBytes)
 	}
 
 	return len(p), nil
@@ -282,7 +277,15 @@ func (g *TermManager) Close() {
 func (g *TermManager) GetRecentHistory() []byte {
 	g.mu.Lock()
 	defer g.mu.Unlock()
-	data := make([]byte, len(g.history))
+	data := make([]byte, 0, len(g.history))
 	data = append(data, g.history...)
 	return data
 }
+
+func truncateFront(slice []byte, max int) []byte {
+	if len(slice) > max {
+		return slice[len(slice)-max:]
+	}
+
+	return slice
+}
diff --git a/lib/srv/termmanager_test.go b/lib/srv/termmanager_test.go
index feb5667bab47c..d1cdb1c2e2b10 100644
--- a/lib/srv/termmanager_test.go
+++ b/lib/srv/termmanager_test.go
@@ -17,6 +17,7 @@ limitations under the License.
 package srv
 
 import (
+	"crypto/rand"
 	"io"
 	"testing"
 	"time"
@@ -48,3 +49,40 @@ func TestCTRLCCapture(t *testing.T) {
 		t.Fatal("terminateNotifier should've seen an event")
 	}
 }
+
+func TestHistoryKept(t *testing.T) {
+	m := NewTermManager()
+	m.On()
+
+	data := make([]byte, 10000)
+	n, err := rand.Read(data)
+	require.NoError(t, err)
+	require.Equal(t, len(data), n)
+
+	n, err = m.Write(data[:len(data)/2])
+	require.NoError(t, err)
+	require.Equal(t, len(data)/2, n)
+
+	n, err = m.Write(data[len(data)/2:])
+	require.NoError(t, err)
+	require.Equal(t, len(data)/2, n)
+
+	kept := data[len(data)-maxHistoryBytes:]
+	require.Equal(t, m.GetRecentHistory(), kept)
+}
+
+func TestBufferedKept(t *testing.T) {
+	m := NewTermManager()
+
+	data := make([]byte, 20000)
+	n, err := rand.Read(data)
+	require.NoError(t, err)
+	require.Equal(t, len(data), n)
+
+	n, err = m.Write(data)
+	require.NoError(t, err)
+	require.Equal(t, len(data), n)
+
+	kept := data[len(data)-maxPausedHistoryBytes:]
+	require.Equal(t, m.buffer, kept)
+}
diff --git a/tool/tsh/kube.go b/tool/tsh/kube.go
index 73eb9d250179a..59d0a583dc70c 100644
--- a/tool/tsh/kube.go
+++ b/tool/tsh/kube.go
@@ -23,6 +23,7 @@ import (
 	"net"
 	"net/url"
 	"os"
+	"sort"
 	"strconv"
 	"strings"
 	"time"
@@ -489,6 +490,10 @@ func (c *kubeSessionsCommand) run(cf *CLIConf) error {
 		}
 	}
 
+	sort.Slice(filteredSessions, func(i, j int) bool {
+		return filteredSessions[i].GetCreated().Before(filteredSessions[j].GetCreated())
+	})
+
 	printSessions(filteredSessions)
 	return nil
 }