diff --git a/cmd-paste-buffer.c b/cmd-paste-buffer.c
index 36326e1841..269e92f775 100644
--- a/cmd-paste-buffer.c
+++ b/cmd-paste-buffer.c
@@ -54,6 +54,11 @@ cmd_paste_buffer_exec(struct cmd *self, struct cmdq_item *item)
 	size_t			 seplen, bufsize;
 	int			 bracket = args_has(args, 'p');
 
+	if (window_pane_exited(wp)) {
+		cmdq_error(item, "target pane has exited");
+		return (CMD_RETURN_ERROR);
+	}
+
 	bufname = NULL;
 	if (args_has(args, 'b'))
 		bufname = args_get(args, 'b');
diff --git a/cmd-pipe-pane.c b/cmd-pipe-pane.c
index 0fa656ce36..268b51bf15 100644
--- a/cmd-pipe-pane.c
+++ b/cmd-pipe-pane.c
@@ -68,7 +68,7 @@ cmd_pipe_pane_exec(struct cmd *self, struct cmdq_item *item)
 	sigset_t			 set, oldset;
 
 	/* Do nothing if pane is dead. */
-	if (wp->fd == -1 || (wp->flags & PANE_EXITED)) {
+	if (window_pane_exited(wp)) {
 		cmdq_error(item, "target pane has exited");
 		return (CMD_RETURN_ERROR);
 	}
diff --git a/options-table.c b/options-table.c
index 89200b9540..f030f2dbd1 100644
--- a/options-table.c
+++ b/options-table.c
@@ -84,6 +84,9 @@ static const char *options_table_window_size_list[] = {
 static const char *options_table_remain_on_exit_list[] = {
 	"off", "on", "failed", NULL
 };
+static const char *options_table_destroy_unattached_list[] = {
+	"off", "on", "keep-last", "keep-group", NULL
+};
 static const char *options_table_detach_on_destroy_list[] = {
 	"off", "on", "no-detached", "previous", "next", NULL
 };
@@ -483,11 +486,12 @@ const struct options_table_entry options_table[] = {
 	},
 
 	{ .name = "destroy-unattached",
-	  .type = OPTIONS_TABLE_FLAG,
+	  .type = OPTIONS_TABLE_CHOICE,
 	  .scope = OPTIONS_TABLE_SESSION,
+	  .choices = options_table_destroy_unattached_list,
 	  .default_num = 0,
 	  .text = "Whether to destroy sessions when they have no attached "
-		  "clients."
+		  "clients, or keep the last session whether in the group."
 	},
 
 	{ .name = "detach-on-destroy",
diff --git a/proc.c b/proc.c
index 68ab9604e5..7c4805f288 100644
--- a/proc.c
+++ b/proc.c
@@ -93,7 +93,7 @@ proc_event_cb(__unused int fd, short events, void *arg)
 			log_debug("peer %p message %d", peer, imsg.hdr.type);
 
 			if (peer_check_version(peer, &imsg) != 0) {
-				int fd = imsg_get_fd(&imsg);
+				fd = imsg_get_fd(&imsg);
 				if (fd != -1)
 					close(fd);
 				imsg_free(&imsg);
diff --git a/server-fn.c b/server-fn.c
index 50f5a8d9f9..2f649329cb 100644
--- a/server-fn.c
+++ b/server-fn.c
@@ -455,7 +455,8 @@ server_destroy_session(struct session *s)
 void
 server_check_unattached(void)
 {
-	struct session	*s;
+	struct session		*s;
+	struct session_group	*sg;
 
 	/*
 	 * If any sessions are no longer attached and have destroy-unattached
@@ -464,8 +465,23 @@ server_check_unattached(void)
 	RB_FOREACH(s, sessions, &sessions) {
 		if (s->attached != 0)
 			continue;
-		if (options_get_number (s->options, "destroy-unattached"))
-			session_destroy(s, 1, __func__);
+		switch (options_get_number(s->options, "destroy-unattached")) {
+		case 0: /* off */
+			continue;
+		case 1: /* on */
+			break;
+		case 2: /* keep-last */
+			sg = session_group_contains(s);
+			if (sg == NULL || session_group_count(sg) <= 1)
+				continue;
+			break;
+		case 3: /* keep-group */
+			sg = session_group_contains(s);
+			if (sg != NULL && session_group_count(sg) == 1)
+				continue;
+			break;
+		}
+		session_destroy(s, 1, __func__);
 	}
 }
 
diff --git a/tmux.1 b/tmux.1
index 10f7317642..9c02835267 100644
--- a/tmux.1
+++ b/tmux.1
@@ -4026,10 +4026,20 @@ The value is the width and height separated by an
 character.
 The default is 80x24.
 .It Xo Ic destroy-unattached
-.Op Ic on | off
+.Op Ic off | on | keep-last | keep-group
 .Xc
-If enabled and the session is no longer attached to any clients, it is
-destroyed.
+If
+.Ic on ,
+destroy the session after the last client has detached.
+If
+.Ic off
+(the default), leave the session orphaned.
+If
+.Ic keep-last ,
+destroy the session only if it is in a group and has other sessions in that group.
+If
+.Ic keep-group ,
+destroy the session unless it is in a group and is the only session in that group.
 .It Xo Ic detach-on-destroy
 .Op Ic off | on | no-detached | previous | next
 .Xc
diff --git a/tmux.h b/tmux.h
index 53f73b20fc..a50adbfae0 100644
--- a/tmux.h
+++ b/tmux.h
@@ -3096,6 +3096,7 @@ int		 window_pane_key(struct window_pane *, struct client *,
 		     struct session *, struct winlink *, key_code,
 		     struct mouse_event *);
 int		 window_pane_visible(struct window_pane *);
+int		 window_pane_exited(struct window_pane *);
 u_int		 window_pane_search(struct window_pane *, const char *, int,
 		     int);
 const char	*window_printable_flags(struct winlink *, int);
diff --git a/window.c b/window.c
index 81d0f809bc..77ce41d8f7 100644
--- a/window.c
+++ b/window.c
@@ -1214,6 +1214,12 @@ window_pane_visible(struct window_pane *wp)
 	return (wp == wp->window->active);
 }
 
+int
+window_pane_exited(struct window_pane *wp)
+{
+	return (wp->fd == -1 || (wp->flags & PANE_EXITED));
+}
+
 u_int
 window_pane_search(struct window_pane *wp, const char *term, int regex,
     int ignore)