diff --git a/lib/client/session.go b/lib/client/session.go
index 71f4584bddf2d..63936b0ea9a7d 100644
--- a/lib/client/session.go
+++ b/lib/client/session.go
@@ -225,22 +225,22 @@ func (ns *NodeSession) createServerSession(ctx context.Context) (*tracessh.Sessi
 		return nil, trace.Wrap(err)
 	}
 
-	envs := map[string]string{}
-
 	// pass language info into the remote session.
 	langVars := []string{"LANG", "LANGUAGE"}
 	for _, env := range langVars {
 		if value := os.Getenv(env); value != "" {
-			envs[env] = value
+			err = sess.Setenv(ctx, env, value)
+			if err != nil {
+				log.Warn(err)
+			}
 		}
 	}
 	// pass environment variables set by client
 	for key, val := range ns.env {
-		envs[key] = val
-	}
-
-	if err := sess.SetEnvs(ctx, envs); err != nil {
-		log.Warn(err)
+		err = sess.Setenv(ctx, key, val)
+		if err != nil {
+			log.Warn(err)
+		}
 	}
 
 	// if agent forwarding was requested (and we have a agent to forward),
diff --git a/lib/srv/forward/sshserver.go b/lib/srv/forward/sshserver.go
index 2b1bbe867750b..ad587d3888c0e 100644
--- a/lib/srv/forward/sshserver.go
+++ b/lib/srv/forward/sshserver.go
@@ -1101,8 +1101,13 @@ func (s *Server) dispatch(ctx context.Context, ch ssh.Channel, req *ssh.Request,
 	case sshutils.PuTTYWinadjRequest:
 		return s.handlePuTTYWinadj(ch, req)
 	default:
-		return trace.BadParameter(
-			"%v doesn't support request type '%v'", s.Component(), req.Type)
+		s.log.Warnf("%v doesn't support request type '%v'", s.Component(), req.Type)
+		if req.WantReply {
+			if err := req.Reply(false, nil); err != nil {
+				s.log.Errorf("sending error reply on SSH channel: %v", err)
+			}
+		}
+		return nil
 	}
 }
 
diff --git a/lib/srv/regular/sshserver.go b/lib/srv/regular/sshserver.go
index b346136ca5244..1f6bfefc59ddc 100644
--- a/lib/srv/regular/sshserver.go
+++ b/lib/srv/regular/sshserver.go
@@ -1564,8 +1564,13 @@ func (s *Server) dispatch(ctx context.Context, ch ssh.Channel, req *ssh.Request,
 			s.Logger.Debugf("%v: deliberately ignoring request for '%v' channel", s.Component(), sshutils.PuTTYSimpleRequest)
 			return nil
 		default:
-			return trace.BadParameter(
-				"(%v) proxy doesn't support request type '%v'", s.Component(), req.Type)
+			s.Logger.Warnf("(%v) proxy doesn't support request type '%v'", s.Component(), req.Type)
+			if req.WantReply {
+				if err := req.Reply(false, nil); err != nil {
+					s.Logger.Errorf("sending error reply on SSH channel: %v", err)
+				}
+			}
+			return nil
 		}
 	}
 
@@ -1662,8 +1667,13 @@ func (s *Server) dispatch(ctx context.Context, ch ssh.Channel, req *ssh.Request,
 	case sshutils.PuTTYWinadjRequest:
 		return s.handlePuTTYWinadj(ch, req)
 	default:
-		return trace.BadParameter(
-			"%v doesn't support request type '%v'", s.Component(), req.Type)
+		s.Logger.Warnf("%v doesn't support request type '%v'", s.Component(), req.Type)
+		if req.WantReply {
+			if err := req.Reply(false, nil); err != nil {
+				s.Logger.Errorf("sending error reply on SSH channel: %v", err)
+			}
+		}
+		return nil
 	}
 }
 
diff --git a/lib/srv/regular/sshserver_test.go b/lib/srv/regular/sshserver_test.go
index 3b6025e1a6e0a..dac7ddf2fe4b6 100644
--- a/lib/srv/regular/sshserver_test.go
+++ b/lib/srv/regular/sshserver_test.go
@@ -1694,6 +1694,30 @@ func TestEnvs(t *testing.T) {
 	}
 }
 
+// TestUnknownRequest validates that any unknown session
+// requests do not terminate the session.
+func TestUnknownRequest(t *testing.T) {
+	t.Parallel()
+	ctx := context.Background()
+
+	f := newFixtureWithoutDiskBasedLogging(t)
+
+	se, err := f.ssh.clt.NewSession(ctx)
+	require.NoError(t, err)
+	defer se.Close()
+
+	// send a random request that won't be handled
+	ok, err := se.SendRequest(ctx, uuid.NewString(), true, nil)
+	require.NoError(t, err)
+	require.False(t, ok)
+
+	// ensure the session is still active
+	require.NoError(t, se.Setenv(ctx, "HOME_TEST", "/test"))
+	output, err := se.Output(ctx, "env")
+	require.NoError(t, err)
+	require.Contains(t, string(output), "HOME_TEST=/test")
+}
+
 // TestNoAuth tries to log in with no auth methods and should be rejected
 func TestNoAuth(t *testing.T) {
 	t.Parallel()
diff --git a/lib/srv/term.go b/lib/srv/term.go
index c714bd82fed63..16d179ef491a7 100644
--- a/lib/srv/term.go
+++ b/lib/srv/term.go
@@ -693,7 +693,9 @@ func (t *remoteTerminal) prepareRemoteSession(ctx context.Context, session *trac
 		teleport.SSHSessionID:           string(scx.SessionID()),
 	}
 
-	if err := session.SetEnvs(ctx, envs); err != nil {
-		t.log.WithError(err).Debug("Unable to set environment variables")
+	for k, v := range envs {
+		if err := session.Setenv(ctx, k, v); err != nil {
+			t.log.Debugf("Unable to set environment variable: %v: %v", k, v)
+		}
 	}
 }