Catching up from an ancient version

Remote Support and Access
1

Good day.
For a number of reasons, I’ve had to hold off on upgrading our Simple Help server. We are currently running 5.3.9 on a Windows 2016 server. I know we are quite a ways behind and know we need to update.
Questions:
-Past conventional wisdom has been to upgrade 1 version at a time. I understand the thinking, but it seems like an arduous set of steps. Thoughts or suggestions on the best way from point A to point B?
-5.3.9 has been quite stable for us, but we’re seeing an uptick in incidents of Windows Defender and other antivirus interfering with all three products (client access, tech, and persistent connection. I also see some of the newer versions (5.5.x families) having similar issues. Is there a version that seems to be more security-software friendly?
-Along the same lines, some of the newer versions seem to have some stability issues. Comments along this thread?
Thanks, all!

2

Can’t comment on the upgrade path, but on your other points.

  • Currently running 5.5.2 and it’s been stable for us, server and client upgrades all completed with issue. We do have the error where technician console reports a version mismatch after reconnecting from sleep state, but that’s been fixed in 5.5.3.
  • With 5.4.x we were having issues with the service occasionally being flagged as malware by Bitdefender and Windows Defender, but haven’t encountered this since upgrading to 5.5.2.
    We’re running the Simple-Help server on Windows Server 2016.