A very venerable app (original version perhaps 15 years ago) is still running on a client's Windows box, every night, processing data and emailing a report.

The email is sent using Shao Sean's libSMTP library, which has performed faithfully for all these years. Unfortunately, the client's replacing their local smtp server with outlook365.com - which requires TLS authentication - which I don't believe libSMTP supports.

The current version of the app is built in LiveCode 6.7.11. There is a huge amount of text to be processed, and - as you might imagine after this long development, with regular changes and additions - the processing is very complex. A few years ago I did look at rebuilding it in LC 8/9, but because of the changes to unicode handling there was a lot of perturbation in the data, and there wasn't time/budget to track all this down in order to get a reasonable new version. I still occasionally need to make tweaks to the processing, but I do that in my trusty LC 6.7.11.

So now I've hit a problem. There still isn't budget for a major exercise to rebuild it in a modern version of LiveCode, so I can't just switch to using tsNet.

Is it theoretically possibly to tweak libSMTP to work with TLS, or is there some basic limitation with LC 6.7 that would make that impossible? Are there any other libraries that work with TLS? Or (I'm not a Windows person) is there some simple way I could set up a local SMTP server on the Windows box that would accept the email from my LiveCode app and forward it to outlook365?

Any suggestions or experience gratefully received.

Ben

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