How to get legit software updates through gauntlet of institutional / corporate anti-malw...

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At $dayjob, we've created some software over the years that performs
rudimentary checks on our web server to see if there are any updates to

At first, we simply munged the .exe extension and that seemed to be good
enough for our software, running on customer PC's, to download and
launch the updates.

But we're seeing more and more Win32 error code 64 showing up in our web
logs when remote clients try to download the updates, so something
running on those customer PC's, or an appliance on their network, is
blocking the download of the update file from our server.

So we're going to try to take a small generic .gif file and pre-pend
that to the front of our update file, and see if that make it through
the anti-malware barriers that we think is in place in these
institutions and corporations.

The users/customers, naturally, have no idea what anti-anything might be
installed on their computer or be operating on their network, so we're
having to become creative to be able get these updates to the client
PC's.  We have no idea what the brand name or product name of any
security product that is likely involved - there is really no way for us
to see or know that from our end.

I'm wondering how this is generally done.  How do purpose-built software
apps get program-code updates (executables, dll's, etc) through what
seems to be barriers like security software running locally, routers
doing deep packet inspection.  ?

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