SSLHandshake failed

Question

Level 1

8 points

SSLHandshake failed

I connect to a proxy based WiFi at my place of work and everything had been working fine before upgrading to 10.10.3. I can connect to WiFi, but I am unable to make a VPN connection using Viscosity (OpenVPN). Before I even start Viscosity, and usually right after entering the username and password for the WiFi proxy, I notice the following error in Console:

4/15/15 10:54:24.639 AM nsurlsessiond[348]: CFNetwork SSLHandshake failed (-9847)

In the Viscosity log, I see the following:

Apr 15 10:53:12: TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)

Apr 15 10:53:12: TLS Error: TLS handshake failed

I'm thinking these two things are related. Thanks!

MacBook Air, Mac OS X (10.7), 1.6 GHz Intel Core 2 Duo with 4 GB

Posted on Apr 15, 2015 8:04 AM

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Answer 1

Shane@shburn Author

Level 1

8 points

Apr 15, 2015 2:01 PM in response to Shane@shburn

I think this more likely a Viscosity issue, as I installed TunnelBlick 3.4.3 and I can now connect to the VPN.

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Answer 2

jkbull

Level 1

86 points

Apr 19, 2015 4:09 AM in response to Shane@shburn

Is there a reason you installed an old version of Tunnelblick? The current stable version is 3.5.0. If you're reluctant to try a ".0", you could use 3.4.4.

The version you are using, 3.4.3, has serious security vulnerabilities – note that the download link is located on Tunnelblick's "Security Risk Downloads" page. For details about the problem, see https://code.google.com/p/tunnelblick/wiki/vulnerability20150319FAQ.

You can update Tunnelblick easily by clicking "Check Now" in the "Updates" section of the "Preferences" panel of Tunnelblick's "VPN Details…" window. While you're there, you might want to consider setting Tunnelblick to check for updates automatically.

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Answer 3

Shane@shburn Author

Level 1

8 points

May 5, 2015 7:56 PM in response to jkbull

Tunnelblick 3.4.3 was the version that was installed before it stopped working. 3.5.0 was the version that started the whole issue as Tunnelblick notified me of an update.

3.4.4 may work, but I was only interested in getting things working again. The location that I am using Tunnelblick, I am unable to ping the server address as it is blocked by the ISP. I suspect that this is likely the difference as Viscosity seemed to not have an option to deal with this case and the logs suggested it couldn't reach the server.

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Answer 4

jkbull

Level 1

86 points

May 5, 2015 8:16 PM in response to Shane@shburn

I'm confused:

Your original post said the problem happened when you switched to Yosemite (apparently using Viscosity).
Your second post said that Tunnelblick 3.4.3 fixed the problem.
Your third post says that Tunnelblick 3.5.0 "started the whole issue" -- what issue? (I thought the issue was connecting to the VPN using Viscosity after you upgraded to Yosemite.)

If Tunnelbick 3.4.3 connects but 3.5.0 doesn't, that could be caused several different things. It should be investigated. Please post to the Tunnelblick Discussion Group (Read Before You Post).

(Edited to change reference to "Mavericks" to "Yosemite".)

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