diff --git a/devel/fossil/Makefile b/devel/fossil/Makefile
index 088eae8d682b..cdd2efdf72ad 100644
--- a/devel/fossil/Makefile
+++ b/devel/fossil/Makefile
@@ -1,55 +1,55 @@
 PORTNAME=	fossil
-PORTVERSION=	2.20
+PORTVERSION=	2.21
 DISTVERSIONPREFIX=	src-
-PORTREVISION=	1
+PORTREVISION=	0
 PORTEPOCH=	2
 CATEGORIES=	devel www
 MASTER_SITES=	https://fossil-scm.org/home/tarball/version-${PORTVERSION}/
 
 MAINTAINER=	gahr@FreeBSD.org
 COMMENT=	DSCM with built-in wiki, http interface and server, tickets database
 WWW=		https://fossil-scm.org/
 
 LICENSE=	BSD2CLAUSE
 LICENSE_FILE=	${WRKSRC}/COPYRIGHT-BSD2.txt
 
 USES=		cpe ssl
 
 WRKSRC=		${WRKDIR}/${PORTNAME}-src-${PORTVERSION}
 
 CPE_VENDOR=	fossil-scm
 HAS_CONFIGURE=	yes
 CONFIGURE_ARGS=	--prefix=${PREFIX} --with-openssl=${OPENSSLBASE}
 USE_RC_SUBR=	fossil
 MAKE_JOBS_UNSAFE=yes
 MAKE_ENV=	TCLSH=${TCLSH}
 
 PLIST_FILES=	bin/fossil man/man1/fossil.1.gz
 
 OPTIONS_DEFINE=	JSON FUSE STATIC TH1HOOKS TCL
 OPTIONS_DEFAULT=JSON
 JSON_DESC=	JSON API support
 FUSE_DESC=	Enable fossil fusefs command
 TH1HOOKS_DESC=	Enable TH1 command and web page hooks
 TCL_DESC=	Enable Tcl integration
 
 JSON_CONFIGURE_ON=	--json
 STATIC_CONFIGURE_ON=	--static
 STATIC_LDFLAGS=		-pthread
 FUSE_CONFIGURE_OFF=	--disable-fusefs
 TH1HOOKS_CONFIGURE_ON=	--with-th1-hooks
 TCL_CONFIGURE_ON=	--with-tcl-stubs --with-tcl=${TCL_LIBDIR}
 TCL_USES=		tcl
 TCL_CFLAGS=		-DTCL_LIBRARY_NAME=\\\"libtcl${TCL_SHLIB_VER}.so\\\" \
 			-DTCL_MINOR_OFFSET=7
 FUSE_LIB_DEPENDS=	libfuse.so:sysutils/fusefs-libs
 FUSE_USES=		localbase:ldflags
 
 post-patch-FUSE-on:
 	@${REINPLACE_CMD} -e 's/define-append LIBS -lfuse/& -pthread/' ${WRKSRC}/auto.def
 
 post-install:
 	@${STRIP_CMD} ${STAGEDIR}${PREFIX}/bin/fossil
 	${INSTALL_MAN} ${WRKSRC}/fossil.1 ${STAGEDIR}${MANPREFIX}/man/man1
 
 .include <bsd.port.mk>
diff --git a/devel/fossil/distinfo b/devel/fossil/distinfo
index 3d0705625de5..3fb9f1b6a7d2 100644
--- a/devel/fossil/distinfo
+++ b/devel/fossil/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1668673291
-SHA256 (fossil-src-2.20.tar.gz) = 0892ea4faa573701ca285a3d4a2d203e8abbb022affe3b1be35658845e8de721
-SIZE (fossil-src-2.20.tar.gz) = 6722255
+TIMESTAMP = 1677736990
+SHA256 (fossil-src-2.21.tar.gz) = 195faf0b20c101834a809979d0a9cdf04a0dcbae1fdabae792c9db900b73bda0
+SIZE (fossil-src-2.21.tar.gz) = 6703622
diff --git a/devel/fossil/files/patch-smtp-ehlo b/devel/fossil/files/patch-smtp-ehlo
new file mode 100644
index 000000000000..eaf809fc494e
--- /dev/null
+++ b/devel/fossil/files/patch-smtp-ehlo
@@ -0,0 +1,39 @@
+Index: src/alerts.c
+==================================================================
+--- src/alerts.c.orig	2023-02-25 19:23:39 UTC
++++ src/alerts.c
+@@ -617,7 +617,7 @@ AlertSender *alert_sender_new(const char *zAltDest, u3
+     if( zRelay ){
+       u32 smtpFlags = SMTP_DIRECT;
+       if( mFlags & ALERT_TRACE ) smtpFlags |= SMTP_TRACE_STDOUT;
+-      p->pSmtp = smtp_session_new(p->zFrom, zRelay, smtpFlags);
++      p->pSmtp = smtp_session_new(smtp_domain_of_addr(p->zFrom), zRelay, smtpFlags);
+       smtp_client_startup(p->pSmtp);
+     }
+   }
+--- src/smtp.c.orig	2023-02-25 19:23:39 UTC
++++ src/smtp.c
+@@ -581,7 +581,7 @@ int smtp_send_msg(
+ ** The input is a base email address of the form "local@domain".
+ ** Return a pointer to just the "domain" part.
+ */
+-static const char *domainOfAddr(const char *z){
++const char *smtp_domain_of_addr(const char *z){
+   while( z[0] && z[0]!='@' ) z++;
+   if( z[0]==0 ) return 0;
+   return z+1;
+@@ -625,12 +625,12 @@ void test_smtp_send(void){
+   zFrom = g.argv[3];
+   nTo = g.argc-4;
+   azTo = (const char**)g.argv+4;
+-  zFromDomain = domainOfAddr(zFrom);
++  zFromDomain = smtp_domain_of_addr(zFrom);
+   if( zRelay!=0 && zRelay[0]!= 0) {
+     smtpFlags |= SMTP_DIRECT;
+     zToDomain = zRelay;
+   }else{
+-    zToDomain = domainOfAddr(azTo[0]);
++    zToDomain = smtp_domain_of_addr(azTo[0]);
+   }
+   p = smtp_session_new(zFromDomain, zToDomain, smtpFlags, smtpPort);
+   if( p->zErr ){