diff --git a/travis/macos-deploy.sh b/travis/macos-deploy.sh
index 2b192b9..91dfe4a 100755
--- a/travis/macos-deploy.sh
+++ b/travis/macos-deploy.sh
@@ -11,3 +11,9 @@ mkdir dist/Syncplay.app/Contents/Resources/es_419.lproj
 pip3 install dmgbuild
 mv syncplay/resources/macOS_readme.pdf syncplay/resources/.macOS_readme.pdf
 dmgbuild -s appdmg.py "Syncplay" dist_bintray/Syncplay_${VER}.dmg
+
+# Workaround for deployment issues with newer openssl.
+# See https://travis-ci.community/t/ruby-openssl-python-deployment-fails-on-osx-image/6753/9
+for lib in ssl crypto; do ln -s /usr/local/opt/openssl{@1.0,}/lib/lib${lib}.1.0.0.dylib; done
+rvm reinstall $(travis_internal_ruby) --disable-binary
+for lib in ssl crypto; do rm /usr/local/opt/openssl/lib/lib${lib}.1.0.0.dylib; done