Let's Encrypt on Mac

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Let's Encrypt on Mac

Postby tetsuo29 » Wed May 05, 2021 4:16 pm

I've been trying and failing to set up SSL using Let's Encrypt on a Mac.

I was trying to follow this recipe.

My Subsonic Server is still running High Sierra (10.13.6)

I was able to install Certbot using Homebrew.

I generated certs using: sudo certbot certonly --standalone

I gave my dyndns.org domain name.

After that, I was able to follow the previously mentioned recipe (I had to install a JDK first).

When I enable https in the /Applications/Subsonic.app/Contents/Info.plist file, all I get when I go to my server is a 404 error.

If I revert back to Subsonic's self signed cert, https works but, of course with the self signed cert warning.

I'd really love to be able to figure out how to use a Let's Encrypt cert with Subsonic on High Sierra. If anyone out there knows how to do this, please help. Thanks.
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Re: Let's Encrypt on Mac

Postby tetsuo29 » Mon May 10, 2021 6:07 pm

Well, after much consternation and trial & error, I figured out how to secure Subsonic using Apache's reverse proxy functionality. This has the added benefit of Certbot being able to automatically generate, download, & install certs. Also, Certbot can then be used to renew certs automatically from a cron job.

I documented what I figured out here so that I would have a head start on the next time I have to do this or in case it can help anyone else.
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Re: Let's Encrypt on Mac

Postby acroyear » Tue May 11, 2021 10:59 pm

sorry, when i saw this post i was swamped for time and couldn't reply...but yeah, the apache reverse proxy is exactly what i did, so that certbot-apache just magically works with no arguments.

if you have your own domain, the reverse proxy might mean that your X.subsonic.org address won't work right, so links to shares may need to be edited before you hand them out. Otherwise, it works quite well.
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