The upstream dev has made this patch, so I've gone ahead and added it to
patches/ here pending the next release. It works for me, though I'm not
sure why I never experienced the issue since I just have LibreSSL 3.2.1
from a recent snapshot.

---
 www/py-httpie/Makefile                        |  7 +++----
 www/py-httpie/distinfo                        |  4 ++--
 www/py-httpie/patches/patch-tests_test_ssl_py | 19 +++++++++++++++++++
 www/py-httpie/pkg/PLIST                       |  4 ++++
 4 files changed, 28 insertions(+), 6 deletions(-)
 create mode 100644 www/py-httpie/patches/patch-tests_test_ssl_py

diff --git a/www/py-httpie/Makefile b/www/py-httpie/Makefile
index d9428c83e86..86c39721853 100644
--- a/www/py-httpie/Makefile
+++ b/www/py-httpie/Makefile
@@ -2,11 +2,10 @@
 
 COMMENT =      command-line HTTP client
 
-MODPY_EGG_VERSION =    2.1.0
+MODPY_EGG_VERSION =    2.2.0
 GH_TAGNAME =           ${MODPY_EGG_VERSION}
-GH_ACCOUNT =           jkbrzt
+GH_ACCOUNT =           jakubroztocil
 GH_PROJECT =           httpie
-DISTNAME =             httpie-${MODPY_EGG_VERSION}
 
 CATEGORIES =           www net
 
@@ -32,7 +31,7 @@ PORTHOME =            ${WRKSRC}
 pre-test:
        # check for docutils presence then calls rst2pseudoxml.py
        # our docutils installs rst2pseudoxml
-       rm ${WRKSRC}/tests/test_docs.py
+       rm -f ${WRKSRC}/tests/test_docs.py
 
 post-install:
        ${INSTALL_DATA_DIR} ${PREFIX}/share/doc/httpie
diff --git a/www/py-httpie/distinfo b/www/py-httpie/distinfo
index 9414d8a17c9..af2bf720bef 100644
--- a/www/py-httpie/distinfo
+++ b/www/py-httpie/distinfo
@@ -1,2 +1,2 @@
-SHA256 (httpie-2.1.0.tar.gz) = rqSC2gk0Gj0gV2HYKMcSWITJ0Ot3pTzU0uYELkZwGCs=
-SIZE (httpie-2.1.0.tar.gz) = 1754801
+SHA256 (httpie-2.2.0.tar.gz) = QTiUrZ1dRaKng5B53NwPI7DqNYZQLVAUM5uVfec9QT4=
+SIZE (httpie-2.2.0.tar.gz) = 1761927
diff --git a/www/py-httpie/patches/patch-tests_test_ssl_py 
b/www/py-httpie/patches/patch-tests_test_ssl_py
new file mode 100644
index 00000000000..ee4c6a9eeaf
--- /dev/null
+++ b/www/py-httpie/patches/patch-tests_test_ssl_py
@@ -0,0 +1,19 @@
+$OpenBSD$
+
+Fix test_ciphers_none_can_be_selected test (patch from upstream)
+Author: Jakub Roztocil <[email protected]>
+
+Index: tests/test_ssl.py
+--- tests/test_ssl.py.orig
++++ tests/test_ssl.py
+@@ -133,4 +133,9 @@ def test_ciphers_none_can_be_selected(httpbin_secure):
+         tolerate_error_exit_status=True,
+     )
+     assert r.exit_status == ExitStatus.ERROR
+-    assert 'No cipher can be selected.' in r.stderr
++    # Linux/macOS:
++    #   http: error: SSLError: ('No cipher can be selected.',)
++    # OpenBSD:
++    #   <https://marc.info/?l=openbsd-ports&m=159251948515635&w=2>
++    #   http: error: Error: [('SSL routines', '(UNKNOWN)SSL_internal', 'no 
cipher match')]
++    assert 'cipher' in r.stderr
diff --git a/www/py-httpie/pkg/PLIST b/www/py-httpie/pkg/PLIST
index 52478a7376f..12d26e1c130 100644
--- a/www/py-httpie/pkg/PLIST
+++ b/www/py-httpie/pkg/PLIST
@@ -22,6 +22,7 @@ 
lib/python${MODPY_VERSION}/site-packages/httpie/${MODPY_PYCACHE}core.${MODPY_PYC
 
lib/python${MODPY_VERSION}/site-packages/httpie/${MODPY_PYCACHE}downloads.${MODPY_PYC_MAGIC_TAG}pyc
 
lib/python${MODPY_VERSION}/site-packages/httpie/${MODPY_PYCACHE}models.${MODPY_PYC_MAGIC_TAG}pyc
 
lib/python${MODPY_VERSION}/site-packages/httpie/${MODPY_PYCACHE}sessions.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/httpie/${MODPY_PYCACHE}ssl.${MODPY_PYC_MAGIC_TAG}pyc
 
lib/python${MODPY_VERSION}/site-packages/httpie/${MODPY_PYCACHE}status.${MODPY_PYC_MAGIC_TAG}pyc
 
lib/python${MODPY_VERSION}/site-packages/httpie/${MODPY_PYCACHE}utils.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/httpie/cli/
@@ -76,10 +77,13 @@ 
lib/python${MODPY_VERSION}/site-packages/httpie/plugins/${MODPY_PYCACHE}__init__
 
lib/python${MODPY_VERSION}/site-packages/httpie/plugins/${MODPY_PYCACHE}base.${MODPY_PYC_MAGIC_TAG}pyc
 
lib/python${MODPY_VERSION}/site-packages/httpie/plugins/${MODPY_PYCACHE}builtin.${MODPY_PYC_MAGIC_TAG}pyc
 
lib/python${MODPY_VERSION}/site-packages/httpie/plugins/${MODPY_PYCACHE}manager.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/httpie/plugins/${MODPY_PYCACHE}registry.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/httpie/plugins/base.py
 lib/python${MODPY_VERSION}/site-packages/httpie/plugins/builtin.py
 lib/python${MODPY_VERSION}/site-packages/httpie/plugins/manager.py
+lib/python${MODPY_VERSION}/site-packages/httpie/plugins/registry.py
 lib/python${MODPY_VERSION}/site-packages/httpie/sessions.py
+lib/python${MODPY_VERSION}/site-packages/httpie/ssl.py
 lib/python${MODPY_VERSION}/site-packages/httpie/status.py
 lib/python${MODPY_VERSION}/site-packages/httpie/utils.py
 share/doc/httpie/
-- 
2.27.0

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