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I'm sorry I've read all the answers and nothing has worked for me...

gem install bundler 
> ERROR:  While executing gem ... (Gem::Exception)
    Unable to require openssl, install OpenSSL and rebuild ruby (preferred) or use 
    non-HTTPS sources

I just upgraded to OSX Mojave 10.14.6. I had OpenSSL before I tried to install Ruby with rvm (per answers here). But just in case, per the answers here, I installed it with an openssl flag like so:

rvm reinstall 2.2.0 --with-openssl-dir=`brew --prefix openssl`

No errors during the install process

I have also tried to uninstall/install with flag --disable-binary as per this answer. The other answers I didn't try, because like... fundamentally if the issue is that you need to have OpenSSL to build Ruby... that's what I'm doing. The other ones that require other commands, I'm not sure what they do so I don't want to just randomly punch them in. Though for lolz I tried with one solution and it didn't help me either.

james
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  • I had the same issues when I updated my os too. I can't remember what I did. I think I followed suggestions here but again, I can't remember totally. https://github.com/rvm/rvm/issues/4357 – Int'l Man Of Coding Mystery Jan 31 '20 at 12:57

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