I was also able to get SFTP working again by manually downgrading to 2.8 as described above. Thanks for that tip. However, then macOS complained about having an old version, and constantly wanted me to upgrade, which is annoying. So, I dug in to why 2.9 wouldn't work with SFTP. Warning: technical details ahead! This won't be a slam dunk if you're not comfortable on the command line, or if you don't want to install homebrew. macOS 10.14.6 ships with version 7.54.0 of curl / libcurl, which you can see by running curl -V in Terminal: $ curl -V curl 7.54.0 (x86_64-apple-darwin18.0) libcurl/7.54.0 LibreSSL/2.6.5 zlib/1.2.11 nghttp2/1.24.1 Protocols: dict file ftp ftps gopher http https imap imaps ldap ldaps pop3 pop3s rtsp smb smbs smtp smtps telnet tftp Features: AsynchDNS IPv6 Largefile GSS-API Kerberos SPNEGO NTLM NTLM_WB SSL libz HTTP2 UnixSockets HTTPS-proxy You can also see that the version it ships with does NOT include the sftp protocol (it would have been included on the Protocols line above). Does Skitch embed libcurl, or does it use the macOS provided version? We can check, and it turns out it "links" against the macOS shipped version, and does not include its own version. This is good, because maybe we can get it to use a version that includes sftp! $ otool -L /Applications/Skitch.app/Contents/MacOS/Skitch | grep -i curl /usr/lib/libcurl.4.dylib (compatibility version 7.0.0, current version 9.0.0) What happens if we install our own version of curl/libcurl, and tell Skitch to use that instead of the macOS provided version? Will it work? Turns out yes, it does, for me. First, install an alternate version of curl using homebrew (google it), or some other method, and find the directory where your new library is installed, like for instance as follows. Version numbers will almost certainly differ for you. $ brew install curl $ ls /usr/local/Cellar/curl/7.73.0/lib libcurl.4.dylib libcurl.a libcurl.dylib pkgconfig Second, quit Skitch completely, including the part that runs in the menu bar. Then, start Skitch on the command line: $ DYLD_LIBRARY_PATH=/usr/local/Cellar/curl/7.73.0/lib /Applications/Skitch.app/Contents/MacOS/Skitch & If the version of curl you just installed includes sftp, then it should work. At least it did for me. And should, as long as the interface to libcurl doesn't change between what it expects in 7.54.0, and what it gets with the version you install (in my case, 7.73.0). This will likely be the case for a while, but not indefinitely. Downside: you always need to start it from the command line with that DYLD_LIBRARY_PATH bit before it. Remove it from your Login Items because as long as you don't start it with that PATH in there, it'll get the version of libcurl, without sftp, that comes with macOS. Yeah, that sucks. It's worth the hassle for me and my workflow. Maybe not for you. Finally, the bold among you may try to make that DYLD_LIBRARY_PATH change system wide, or overwrite the version of libcurl that exists in /usr/lib. I'm not that adventerous.