diff --git a/audio/shairport-sync/Makefile b/audio/shairport-sync/Makefile
index 9ff023c4ea26..e73cf45f65ae 100644
--- a/audio/shairport-sync/Makefile
+++ b/audio/shairport-sync/Makefile
@@ -1,73 +1,75 @@
 PORTNAME=	shairport-sync
-DISTVERSION=	5.2.3
+DISTVERSION=	5.5
 CATEGORIES=	audio
 
 MAINTAINER=	ehaupt@FreeBSD.org
 COMMENT=	AirPlay audio player with multi-room audio synchronisation capability
 WWW=		https://github.com/mikebrady/shairport-sync
 
 LICENSE=	BSD3CLAUSE
 
 LIB_DEPENDS=	libavahi-client.so:net/avahi-app \
 		libconfig.so:devel/libconfig \
 		libdaemon.so:devel/libdaemon \
 		libpopt.so:devel/popt \
 		libsoxr.so:audio/libsoxr
 
 USES=		autoreconf libtool localbase pkgconfig ssl
 USE_GITHUB=	yes
 GH_ACCOUNT=	mikebrady
 USE_RC_SUBR=	${PORTNAME}
 
 GNU_CONFIGURE=	yes
 CONFIGURE_ARGS=	--sysconfdir=${LOCALBASE}/etc \
 		--with-avahi \
 		--with-libdaemon \
 		--with-metadata \
 		--with-piddir=/var/run/shairport-sync \
 		--with-pipe \
 		--with-soxr \
 		--with-ssl=openssl \
 		--with-stdout
 CONFIGURE_ENV+=	SSL_CFLAGS=-I${OPENSSLINC} \
 		SSL_LIBS=-L${OPENSSLLIB}
 
 LDFLAGS+=	-lcrypto
 
+SUB_FILES=	pkg-message
+
 OPTIONS_DEFINE=		AIRPLAY2 ALAC ALSA MQTT PULSEAUDIO SNDIO
-OPTIONS_DEFAULT=	AIRPLAY2
+OPTIONS_DEFAULT=	AIRPLAY2 SNDIO
+OPTIONS_SUB=		yes
 AIRPLAY2_DESC=		Build with AirPlay 2 protocol support
 ALAC_DESC=		Build with libalac support (experimental)
 MQTT_DESC=		Build with MQTT protocol support
-SNDIO_DESC=		Sndio audio support (DEPRECATED upstream)
+SNDIO_DESC=		Sndio audio support
 
 AIRPLAY2_BUILD_DEPENDS=	vim:editors/vim
 AIRPLAY2_LIB_DEPENDS=	libavutil.so:multimedia/ffmpeg \
 			libgcrypt.so:security/libgcrypt \
 			libplist-2.0.so:devel/libplist \
 			libsodium.so:security/libsodium \
 			libuuid.so:misc/libuuid
 AIRPLAY2_RUN_DEPENDS=	nqptp:net/nqptp
 AIRPLAY2_CONFIGURE_ON=	--with-airplay-2
-AIRPLAY2_SUB_FILES=	pkg-message
 
 ALAC_LIB_DEPENDS=	libalac.so:audio/alac
 ALAC_CONFIGURE_ON=	--with-apple-alac
 
 ALSA_LIB_DEPENDS=	libasound.so:audio/alsa-lib
 ALSA_CONFIGURE_ON=	--with-alsa
 
 MQTT_LIB_DEPENDS=	libmosquitto.so:net/mosquitto
 MQTT_CONFIGURE_ON=	--with-mqtt-client
 
 PULSEAUDIO_LIB_DEPENDS=		libpulse.so:audio/pulseaudio
 PULSEAUDIO_CONFIGURE_ON=	--with-pa
 
 SNDIO_LIB_DEPENDS=	libsndio.so:audio/sndio
 SNDIO_CONFIGURE_ON=	--with-sndio
 
 post-patch:
 	@${REINPLACE_CMD} -e 's/-Wno-clobbered -Wno-psabi //' \
 		${WRKSRC}/Makefile.am
 
 .include <bsd.port.mk>
diff --git a/audio/shairport-sync/distinfo b/audio/shairport-sync/distinfo
index d7043143ee49..ad6d9f7f3592 100644
--- a/audio/shairport-sync/distinfo
+++ b/audio/shairport-sync/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1787858778
-SHA256 (mikebrady-shairport-sync-5.2.3_GH0.tar.gz) = 890eacbcba979a1f20ba92076310757a01adaa03161713c6d603d9bd54ba8898
-SIZE (mikebrady-shairport-sync-5.2.3_GH0.tar.gz) = 647139
+TIMESTAMP = 1788769523
+SHA256 (mikebrady-shairport-sync-5.5_GH0.tar.gz) = 5fcce2ee6b6fbda5fcfb381d0000ab799ec7ce4c285098da6bef82a17237945f
+SIZE (mikebrady-shairport-sync-5.5_GH0.tar.gz) = 647803
diff --git a/audio/shairport-sync/files/pkg-message.in b/audio/shairport-sync/files/pkg-message.in
index 4bad0dc95f7f..1e1a9c66829f 100644
--- a/audio/shairport-sync/files/pkg-message.in
+++ b/audio/shairport-sync/files/pkg-message.in
@@ -1,11 +1,38 @@
-[   
+[
 { type: install
-  message: <<EOM
+message: <<EOM
 
-Shairport sync is using AirPlay 2. Please make sure you enable and start nqptp.
-
-    # sysrc nqptp_enable=YES
-    # service nqptp start
+%%AIRPLAY2%%Shairport Sync is using AirPlay 2. Please make sure you enable and start nqptp.
+%%AIRPLAY2%%
+%%AIRPLAY2%%# sysrc nqptp_enable=YES
+%%AIRPLAY2%%# service nqptp start
+%%AIRPLAY2%%
+%%SNDIO%%The sndio "default" device does not necessarily correspond to the
+%%SNDIO%%default FreeBSD sound device shown by /dev/sndstat. If Shairport Sync
+%%SNDIO%%is visible to AirPlay clients but exits when playback starts with an
+%%SNDIO%%error such as:
+%%SNDIO%%
+%%SNDIO%%output configuration search for request: S16/44100/2 failed
+%%SNDIO%%
+%%SNDIO%%check the available sound devices with:
+%%SNDIO%%
+%%SNDIO%%# cat /dev/sndstat
+%%SNDIO%%
+%%SNDIO%%and explicitly select the desired sndio device in:
+%%SNDIO%%
+%%SNDIO%%%%PREFIX%%/etc/shairport-sync.conf
+%%SNDIO%%
+%%SNDIO%%For example, if the desired device corresponds to rsnd/8:
+%%SNDIO%%
+%%SNDIO%%sndio =
+%%SNDIO%%{
+%%SNDIO%% device = "rsnd/8";
+%%SNDIO%% output_rate = 48000;
+%%SNDIO%% output_format = "S16_LE";
+%%SNDIO%% output_channels = 2;
+%%SNDIO%%};
+%%SNDIO%%
+%%SNDIO%%Adjust the rsnd device number as appropriate for the system.
 EOM
 }
 ]