This is not a case for a client but clients since we are talking about vertical market application with many users.
But building a wrapper around wwIpStuff and wwSmtp is something I will consider (when time permits).
Thank you.

>I think you/your client should reconsider. Old wwIPstuff used the OS Internet functions, which did not have hooks for crypto back when I needed such stuff, otherwise I would have gladly used Ricks sources. My GUESS! is, that the need to use .Net comes for ***all*** crypto needs, so you either include other components allowing crypto to enabled in their interfaces (which inflates install as well) or you stay with Ricks implementation, but make it crystal clear that more and more functionality might be blocked if used from a machine without .Net (create a small wrapper to createobject() new stuff if .Net is available, fall back to wwIPstuff otherwise, allowing you to keep most of your code unchanged.
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>Mail providers block non SSL here about everywhere, Google will filter out non-HTTPS: sites soon and so on.
>As you call into RPC or SOAP/REST, SSL and/or certificate added capabilities should be in your arsenal ;-)
>
>Verify on West-Wind before ripping out/plunging $ for new stuff
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>;-)
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>>I actually did buy the WestWindClient Tools. But I cannot use it in this project because it requires .NET frameworks to be installed on the computer. Some customers may not want to go through the installation of .NET. So until I can be assured that each customer will install .NET on their computer, I have to stay with the old wwIpStuff.
>>
>>>If you're using GMail you need TLS. The old wwIpstuff library doesn't support that. The newer wwSmtp library that's part of the West Wind Client Tools (https://west-wind.com/WestwindClientTools.aspx) supports it and it has the **same** interface as wwipstuff - you basically just change the class name. wwIPstuff is so old there wasn't even and official TLS authenticated protocol at the time, so probably time to upgrade to something a little more modern :-)
>>>
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>>>There's an example in the documentation that shows how to send email with Gmail specifically:
>>>
>>>Sending TLS Emails with GMail
>>>
>>>+++ Rick ---
>>>
>>>>Hi,
>>>>
>>>>I am trying to send email using GMAIL server. For SMTP I use "smtp.gmail.com", port 465, and then user gmail user ID and password.
>>>>But I get a message "cannot connect to the server"
>>>>Is there a setting or something I am missing?
>>>>
>>>>TIA