As the title says, when I try to install packages via homebrew through my home network, I get the following error:

curl: (35) LibreSSL SSL_connect: SSL_ERROR_SYSCALL in connection to akamai.bintray.com:443 
Error: Failed to download resource "rclone"
Download failed: https://homebrew.bintray.com/bottles/rclone-1.38.high_sierra.bottle.tar.gz

However, I can download from the .tar.gz URL that is specified just fine through my browser.

I know this is only a problem with my home network because when I tether my phone it works fine.

Probably got something to do with my router settings and/or ISP but I am not sure where to look.

Thanks for the help! :)

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    Did you ever figure this out? I'm seeing the same issue and it is also limited to my home network. – Alexander Ekdahl Feb 4 '18 at 3:14
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    Nope, I just use another network for this stuff :( – philosopher Feb 5 '18 at 4:22
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    I managed to fix it by adding --ciphers ECDHE-RSA-AES128-GCM-SHA256 to the curl request. Another solution is to download a newer version curl. – Alexander Ekdahl Feb 25 '18 at 23:27
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    Thanks man, how did you figure it out? Also can you tell me which curl version you installed to get it working, because I got the latest version and its still not working :( I'm on Mac OSX – philosopher Mar 1 '18 at 16:23
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    @AlexanderEkdahl do you why this happens by any chance? I am curious – philosopher Mar 2 '18 at 18:00

A thought occurs to me -- have you checked your router to see if it is doing a transparent proxy for you?

If it is, then you may want to turn that off.

If you can't turn it off, then you might want to install a VPN solution that will allow you to bypass it.

Just a thought.

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    this was the problem for me - thanks – Franco Jun 26 '18 at 21:14
  • Thanks. By the router acting as a transparent proxy, I guess it means all my requests are intercepted by the router? Is this a security risk even if my traffic is https encrypted? – philosopher Sep 27 '18 at 8:45

Since you're using LibreSSL, try re-installing curl with OpenSSL instead of Secure Transport.

The latest brew, it depends on OpenSSL by default, so you've to reinstall it:

brew reinstall curl

For older Brew, there was an option --with-openssl which was removed, e.g.

brew reinstall curl --with-openssl

Here are few other suggestions:

  • Run brew options curl to display install options specific to formula.
  • Compile from the source. Check curl.rb formula for more details.
  • Make sure you're not using http_proxy/https_proxy.
  • Use -v to curl for more verbose output.
  • Try using BSD curl at /usr/bin/curl, run which -a curl to list them all.
  • Make sure you haven't accidentally blocked curl in your firewall (such as Little Snitch).
  • Alternatively use wget.
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  • brew reinstall curl --with-openssl get Error: invalid option: --with-openssl – Jeff Tian Mar 15 '19 at 10:07
  • Check brew options curl to display install options specific to formula, as per manual. – kenorb Mar 15 '19 at 13:21
  • Thanks for the reply. But my brew options curl gives empty result. What gives? – Jeff Tian Mar 18 '19 at 2:24
  • It seems the option was removed, try reinstalling it without any option. I've updated the answer. – kenorb Mar 18 '19 at 11:41
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    Try: brew uninstall curl. The one which comes from macOS, you can't uninstall it. You need to install new one in /usr/local and Brew should adjust $PATH, to point to the new one first. – kenorb Mar 19 '19 at 14:07

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