WorldEdit
If you value pragmatism over ideology, then my anecdote may convince you:

It's no secret that Cuberite is not yet stable, and it might have security vulnerabilities. Wise Gnu/Linux server owners should probably run it as a dedicated user, and not as the their default, daily used user. I typically run it as the default user when testing, but my pc is firewalled and no outside users can connect, so security is not a problem.

I wouldn't want it to contact the net and I never expected it to do so. After updating WorldEdit, I found out it was unexpectedly connecting to the net. I am a security-conscious guy, and I wouldn't want a potentially unsecure program to connect to the net as the default user, and it did exactly that, without asking for my permission.
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What LogicParrot said. It might sound a bit over the top, but it's something more people should care about.

Just mention in the release post that an update-checker is available that can be opt-in, if the user wants it. This way you make everybody happy.

Also related to this, a video everyone should watch: https://www.youtube.com/watch?v=Ag1AKIl_2GM (I'm sorry, Youtube, but it's not my video).
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You can even tell the user at the console if you'd like to better advertise this. "Auto update functionality is available, type /we-autoupdate to enable or /we-dismiss to stop this message from appearing".
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If anyone wants my opinion: I love autoupdates! Update away, Windows 10, and WorldEdit too! :D
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@NiLSPACE Does the updater of WorldEdit downloads the new version every time on start / reload of server, regardless of if the downloaded zip file is already available?
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Now that you mention it, yes it does. I should probably fix that and disable the updater by default (since that won in the vote)
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