diff --git a/dev-python/pypy/pypy-4.0.1.ebuild b/dev-python/pypy/pypy-4.0.1.ebuild
index a6c918a540f09..69c51e4563f11 100644
--- a/dev-python/pypy/pypy-4.0.1.ebuild
+++ b/dev-python/pypy/pypy-4.0.1.ebuild
@@ -17,13 +17,14 @@ SRC_URI="https://bitbucket.org/pypy/pypy/downloads/${P}-src.tar.bz2
 LICENSE="MIT"
 SLOT="0/$(get_version_component_range 1-2 ${PV})"
 KEYWORDS="~amd64 ~x86 ~amd64-linux ~x86-linux"
-IUSE="bzip2 doc gdbm +jit low-memory ncurses sandbox +shadowstack sqlite cpu_flags_x86_sse2 test tk"
+IUSE="bzip2 doc gdbm +jit libressl low-memory ncurses sandbox +shadowstack sqlite cpu_flags_x86_sse2 test tk"
 
 RDEPEND=">=sys-libs/zlib-1.1.3:0=
 	virtual/libffi:0=
 	virtual/libintl:0=
 	dev-libs/expat:0=
-	dev-libs/openssl:0=[-bindist]
+	!libressl? ( dev-libs/openssl:0=[-bindist] )
+	libressl? ( dev-libs/libressl:0= )
 	bzip2? ( app-arch/bzip2:0= )
 	gdbm? ( sys-libs/gdbm:0= )
 	ncurses? ( sys-libs/ncurses:0= )
diff --git a/dev-python/pypy/pypy-5.0.0.ebuild b/dev-python/pypy/pypy-5.0.0.ebuild
index a6c918a540f09..69c51e4563f11 100644
--- a/dev-python/pypy/pypy-5.0.0.ebuild
+++ b/dev-python/pypy/pypy-5.0.0.ebuild
@@ -17,13 +17,14 @@ SRC_URI="https://bitbucket.org/pypy/pypy/downloads/${P}-src.tar.bz2
 LICENSE="MIT"
 SLOT="0/$(get_version_component_range 1-2 ${PV})"
 KEYWORDS="~amd64 ~x86 ~amd64-linux ~x86-linux"
-IUSE="bzip2 doc gdbm +jit low-memory ncurses sandbox +shadowstack sqlite cpu_flags_x86_sse2 test tk"
+IUSE="bzip2 doc gdbm +jit libressl low-memory ncurses sandbox +shadowstack sqlite cpu_flags_x86_sse2 test tk"
 
 RDEPEND=">=sys-libs/zlib-1.1.3:0=
 	virtual/libffi:0=
 	virtual/libintl:0=
 	dev-libs/expat:0=
-	dev-libs/openssl:0=[-bindist]
+	!libressl? ( dev-libs/openssl:0=[-bindist] )
+	libressl? ( dev-libs/libressl:0= )
 	bzip2? ( app-arch/bzip2:0= )
 	gdbm? ( sys-libs/gdbm:0= )
 	ncurses? ( sys-libs/ncurses:0= )
diff --git a/dev-python/pypy/pypy-9999.ebuild b/dev-python/pypy/pypy-9999.ebuild
index 07df847691940..73a3d5309d9cc 100644
--- a/dev-python/pypy/pypy-9999.ebuild
+++ b/dev-python/pypy/pypy-9999.ebuild
@@ -18,13 +18,14 @@ SRC_URI="
 LICENSE="MIT"
 SLOT="0/$(get_version_component_range 1-2 ${PV})"
 KEYWORDS=""
-IUSE="bzip2 doc gdbm +jit low-memory ncurses sandbox +shadowstack sqlite cpu_flags_x86_sse2 test tk"
+IUSE="bzip2 doc gdbm +jit libressl low-memory ncurses sandbox +shadowstack sqlite cpu_flags_x86_sse2 test tk"
 
 RDEPEND=">=sys-libs/zlib-1.1.3:0=
 	virtual/libffi:0=
 	virtual/libintl:0=
 	dev-libs/expat:0=
-	dev-libs/openssl:0=[-bindist]
+	!libressl? ( dev-libs/openssl:0=[-bindist] )
+	libressl? ( dev-libs/libressl:0= )
 	bzip2? ( app-arch/bzip2:0= )
 	gdbm? ( sys-libs/gdbm:0= )
 	ncurses? ( sys-libs/ncurses:0= )