diff --git a/ChangeLog b/ChangeLog
index eb10e1059..e7e1486cd 100644
--- a/ChangeLog
+++ b/ChangeLog
@@ -78,6 +78,10 @@
    - djm@cvs.openbsd.org 2008/02/10 09:55:37
      [sshd_config.5]
      mantion that "internal-sftp" is useful with ForceCommand too
+   - djm@cvs.openbsd.org 2008/02/10 10:54:29
+     [servconf.c session.c]
+     delay ~ expansion for ChrootDirectory so it expands to the logged-in user's
+     home, rather than the user who starts sshd (probably root)
 
 20080119
  - (djm) Silence noice from expr in ssh-copy-id; patch from
@@ -3606,4 +3610,4 @@
    OpenServer 6 and add osr5bigcrypt support so when someone migrates
    passwords between UnixWare and OpenServer they will still work. OK dtucker@
 
-$Id: ChangeLog,v 1.4836 2008/02/10 11:47:24 djm Exp $
+$Id: ChangeLog,v 1.4837 2008/02/10 11:48:55 djm Exp $
diff --git a/servconf.c b/servconf.c
index d38d0bfb1..9add96ca1 100644
--- a/servconf.c
+++ b/servconf.c
@@ -1,4 +1,4 @@
-/* $OpenBSD: servconf.c,v 1.176 2008/02/08 23:24:08 djm Exp $ */
+/* $OpenBSD: servconf.c,v 1.177 2008/02/10 10:54:28 djm Exp $ */
 /*
  * Copyright (c) 1995 Tatu Ylonen <ylo@cs.hut.fi>, Espoo, Finland
  *                    All rights reserved
@@ -1260,7 +1260,14 @@ parse_flag:
 
 	case sChrootDirectory:
 		charptr = &options->chroot_directory;
-		goto parse_filename;
+
+		arg = strdelim(&cp);
+		if (!arg || *arg == '\0')
+			fatal("%s line %d: missing file name.",
+			    filename, linenum);
+		if (*activep && *charptr == NULL)
+			*charptr = xstrdup(arg);
+		break;
 
 	case sDeprecated:
 		logit("%s line %d: Deprecated option %s",
diff --git a/session.c b/session.c
index 1768c8c2f..545e27fb7 100644
--- a/session.c
+++ b/session.c
@@ -1,4 +1,4 @@
-/* $OpenBSD: session.c,v 1.226 2008/02/08 23:24:07 djm Exp $ */
+/* $OpenBSD: session.c,v 1.227 2008/02/10 10:54:29 djm Exp $ */
 /*
  * Copyright (c) 1995 Tatu Ylonen <ylo@cs.hut.fi>, Espoo, Finland
  *                    All rights reserved
@@ -1359,6 +1359,8 @@ safely_chroot(const char *path, uid_t uid)
 void
 do_setusercontext(struct passwd *pw)
 {
+	char *chroot_path, *tmp;
+
 #ifndef HAVE_CYGWIN
 	if (getuid() == 0 || geteuid() == 0)
 #endif /* HAVE_CYGWIN */
@@ -1442,11 +1444,12 @@ do_setusercontext(struct passwd *pw)
 
 		if (options.chroot_directory != NULL &&
 		    strcasecmp(options.chroot_directory, "none") != 0) {
-			char *chroot_path;
-
-			chroot_path = percent_expand(options.chroot_directory,
-			    "h", pw->pw_dir, "u", pw->pw_name, (char *)NULL);
+                        tmp = tilde_expand_filename(options.chroot_directory,
+			    pw->pw_uid);
+			chroot_path = percent_expand(tmp, "h", pw->pw_dir,
+			    "u", pw->pw_name, (char *)NULL);
 			safely_chroot(chroot_path, pw->pw_uid);
+			free(tmp);
 			free(chroot_path);
 		}