Index: lang/crystal/Makefile
===================================================================
--- lang/crystal/Makefile
+++ lang/crystal/Makefile
@@ -1,5 +1,6 @@
 PORTNAME=		crystal
 DISTVERSION=		1.1.1
+PORTREVISION=		1
 CATEGORIES=		lang
 MASTER_SITES=		https://dl.unrelenting.technology/crystal/:bootstrap
 DISTFILES=		${BOOTSTRAP_PATH}:bootstrap
@@ -23,7 +24,7 @@
 		git:devel/git
 RUN_DEPENDS=	pkg-config:devel/pkgconf
 
-USES=		compiler gmake pkgconfig
+USES=		compiler gmake pkgconfig ssl
 
 USE_GITHUB=	yes
 GH_ACCOUNT=	crystal-lang
@@ -52,6 +53,15 @@
 IGNORE=		not supported on anything but FreeBSD
 .endif
 
+# crystal needs pkgconfig to determine SSL variants but these are not
+# present in FreeBSD base. We splice in the correct info based on
+# FreeBSD version and hope it doesn't change during minor releases.
+# See post-patch for the substitutions of these patches.
+.if ${OPSYS} == FreeBSD && ${SSL_DEFAULT} == "base"
+EXTRA_PATCHES=	${PATCHDIR}/extra-patch-src_openssl_lib__crypto.cr \
+		${PATCHDIR}/extra-patch-src_openssl_lib__ssl.cr
+.endif
+
 post-extract:
 	${MKDIR} ${WRKSRC}/.build
 	${CP} ${DISTDIR}/${DIST_SUBDIR}/${BOOTSTRAP_PATH} ${WRKSRC}/.build/crystal
@@ -59,6 +69,23 @@
 	${LN} -s x86_64-freebsd ${WRKSRC}/src/lib_c/aarch64-portbld-freebsd
 	${LN} -s x86_64-freebsd ${WRKSRC}/src/lib_c/aarch64-freebsd
 
+post-patch:
+.if 	${SSL_DEFAULT} == "base" && ${OSVERSION} > 1000000 && ${OSVERSION} < 1200000
+	@${REINPLACE_CMD} \
+		-e 's|CRYSTAL_LIBRESSL_VERSION|0.0.0|g' \
+		-e 's|CRYSTAL_OPENSSL_VERSION|1.0.2|g' \
+		-e 's|CRYSTAL_SSL_LDFLAGS|${OPENSSLLIB}|g' \
+		${WRKSRC}/src/openssl/lib_ssl.cr \
+		${WRKSRC}/src/openssl/lib_crypto.cr
+.elif 	${SSL_DEFAULT} == "base" && ${OSVERSION} > 1100000 && ${OSVERSION} < 1400028
+	@${REINPLACE_CMD} \
+		-e 's|CRYSTAL_LIBRESSL_VERSION|0.0.0|g' \
+		-e 's|CRYSTAL_OPENSSL_VERSION|1.1.1|g' \
+		-e 's|CRYSTAL_SSL_LDFLAGS|${OPENSSLLIB}|g' \
+		${WRKSRC}/src/openssl/lib_ssl.cr \
+		${WRKSRC}/src/openssl/lib_crypto.cr
+.endif
+
 do-build-DOCS-on:
 	cd ${WRKSRC} && ${SETENV} ${MAKE_ENV} ${MAKE_CMD} ${MAKE_ARGS} docs \
 			CRYSTAL_CACHE_DIR="${WRKDIR}/cache"
Index: lang/crystal/files/extra-patch-src_openssl_lib__crypto.cr
===================================================================
--- /dev/null
+++ lang/crystal/files/extra-patch-src_openssl_lib__crypto.cr
@@ -0,0 +1,27 @@
+--- src/openssl/lib_crypto.cr.orig	2021-08-08 15:06:11 UTC
++++ src/openssl/lib_crypto.cr
+@@ -1,21 +1,11 @@
+ {% begin %}
+   lib LibCrypto
+-    {% from_libressl = (`hash pkg-config 2> /dev/null || printf %s false` != "false") &&
+-                       (`test -f $(pkg-config --silence-errors --variable=includedir libcrypto)/openssl/opensslv.h || printf %s false` != "false") &&
+-                       (`printf "#include <openssl/opensslv.h>\nLIBRESSL_VERSION_NUMBER" | ${CC:-cc} $(pkg-config --cflags --silence-errors libcrypto || true) -E -`.chomp.split('\n').last != "LIBRESSL_VERSION_NUMBER") %}
+-    {% ssl_version = `hash pkg-config 2> /dev/null && pkg-config --silence-errors --modversion libcrypto || printf %s 0.0.0`.split.last.gsub(/[^0-9.]/, "") %}
+-
+-    {% if from_libressl %}
+-      LIBRESSL_VERSION = {{ ssl_version }}
+-      OPENSSL_VERSION = "0.0.0"
+-    {% else %}
+-      LIBRESSL_VERSION = "0.0.0"
+-      OPENSSL_VERSION = {{ ssl_version }}
+-    {% end %}
++    LIBRESSL_VERSION = "CRYSTAL_LIBRESSL_VERSION"
++    OPENSSL_VERSION = "CRYSTAL_OPENSSL_VERSION"
+   end
+ {% end %}
+ 
+-@[Link(ldflags: "`command -v pkg-config > /dev/null && pkg-config --libs --silence-errors libcrypto || printf %s '-lcrypto'`")]
++@[Link(ldflags: "-LCRYSTAL_SSL_LDFLAGS -lcrypto")]
+ lib LibCrypto
+   alias Char = LibC::Char
+   alias Int = LibC::Int
Index: lang/crystal/files/extra-patch-src_openssl_lib__ssl.cr
===================================================================
--- /dev/null
+++ lang/crystal/files/extra-patch-src_openssl_lib__ssl.cr
@@ -0,0 +1,28 @@
+--- src/openssl/lib_ssl.cr.orig	2021-08-08 15:06:09 UTC
++++ src/openssl/lib_ssl.cr
+@@ -6,22 +6,12 @@ require "./lib_crypto"
+ 
+ {% begin %}
+   lib LibSSL
+-    {% from_libressl = (`hash pkg-config 2> /dev/null || printf %s false` != "false") &&
+-                       (`test -f $(pkg-config --silence-errors --variable=includedir libssl)/openssl/opensslv.h || printf %s false` != "false") &&
+-                       (`printf "#include <openssl/opensslv.h>\nLIBRESSL_VERSION_NUMBER" | ${CC:-cc} $(pkg-config --cflags --silence-errors libssl || true) -E -`.chomp.split('\n').last != "LIBRESSL_VERSION_NUMBER") %}
+-    {% ssl_version = `hash pkg-config 2> /dev/null && pkg-config --silence-errors --modversion libssl || printf %s 0.0.0`.split.last.gsub(/[^0-9.]/, "") %}
+-
+-    {% if from_libressl %}
+-      LIBRESSL_VERSION = {{ ssl_version }}
+-      OPENSSL_VERSION = "0.0.0"
+-    {% else %}
+-      LIBRESSL_VERSION = "0.0.0"
+-      OPENSSL_VERSION = {{ ssl_version }}
+-    {% end %}
++    LIBRESSL_VERSION = "CRYSTAL_LIBRESSL_VERSION"
++    OPENSSL_VERSION = "CRYSTAL_OPENSSL_VERSION"
+   end
+ {% end %}
+ 
+-@[Link(ldflags: "`command -v pkg-config > /dev/null && pkg-config --libs --silence-errors libssl || printf %s '-lssl -lcrypto'`")]
++@[Link(ldflags: "-LCRYSTAL_SSL_LDFLAGS -lssl")]
+ lib LibSSL
+   alias Int = LibC::Int
+   alias Char = LibC::Char