CheckForOctopusUgrades fails with SSL error

In the middle of evaluating OD and most things looks good so far, but I get this error in the server logs once a day.

ERROR Error when running scheduled task: CheckForOctopusUpgrades
System.Net.WebException: The request was aborted: Could not create SSL/TLS secure channel.
at System.Net.WebClient.DownloadDataInternal(Uri address, WebRequest& request)
at System.Net.WebClient.DownloadString(Uri address)
at Octopus.Server.Schedules.CheckForOctopusUpgrades.CheckForUpdates() in y:\work\refs\heads\release\source\Octopus.Server\Schedules\CheckForOctopusUpgrades.cs:line 90
at Octopus.Server.Schedules.CheckForOctopusUpgrades.Trigger() in y:\work\refs\heads\release\source\Octopus.Server\Schedules\CheckForOctopusUpgrades.cs:line 71
at Octopus.Server.Schedules.Scheduler.RunTask(IRunOnASchedule task) in y:\work\refs\heads\release\source\Octopus.Server\Schedules\Scheduler.cs:line 83

What could cause that?


Thanks for reaching out. What the Octopus server is trying to do, is reach us out to see if there’s any upgrade available for your Octopus server. You might have a firewall/proxy blocking that connection.

If you’d like to set Octopus so it doesn’t automatically look for updates, you can run the following command

cd C:\Program Files\Octopus Deploy\Octopus

Octopus.server.exe config --upgradecheck=false

Hope that helps!


There should not be any proxy/firewall blocking anything on that server.

What address and type of request is it doing for that check? I would like to test manually and se what happens.


Hi Ulf,

The server is trying to reach this address:



I have tried both manually and by scheduling wget to run as the system account and both cases works fine. This is on a W2K12R2 server, an installation on a W2K8R2 server works just fine.

Can’t really figure it out so unless you have something you want me to test I will leave it like that for the moment.


Hi Ulf,

If you’d really like to get to the bottom of the issue, i’d suggest you to leave a web debugger on on that machine waiting for connections to that URL and come back a couple of hours later to see the results (This runs every 4hs). Its ok if you want to leave it that way, it wont cause any major problems.



Ok, like Fiddler with SSL interception active?

But every 4h?, the logs only show one error per day, and never at the same time the last few days…

Hmm… I will put this on ice for a while and observe what happens over time…

Br, Ulf

In our case, we do have a proxy server configured, but if the OctopusDeploy service is running under the Local System account, I am pretty sure it will not see my user setting if I log in and configure the proxy. How can I set the proxy server for the OctopusDeploy service correctly?