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For using GMail, you can't just use the password that you use to login to the account with. You need to setup an application specific password for access.
This is covered in google's documentation "Sign in using App Passwords":
Follow the instructions for "how to generate an app password", then use the password that google generates as the password in filemaker for sending mail.
Thank you Mike, very grateful for your advice.
I can see the "need" to use particular e-ddresses for sending, as we don't have a control over the reply-to and many don't want to send FROM as a 'generic' email (they might expect a reply!).
Have you found any way to get the reply-to set with Send Mail and SMTP?
Use of plug-in or external email services is the only ways I've found.
Not sure if your question was aimed at me or Mike, but if me - no I haven;t yet got on to that!
Sort of both. Were you needing to select different "From" as the sender for a reason? My thoughts were to have a convenient "reply" (the same as From if there is no Reply-to in the headers).
And there is no way that I have seen within the Send Mail script step to make this setting, so I asked Mike's opinions.
When using email from a "group", my recommendation usually is to have a group account that apps can send from (solves that problem) with FileMaker (or websites). And all reply-tos will likely go to that account. Then all of the group can read anything in that mailbox, but don't manually have access to send from that account.
Groups using a domain name, for example, might have an email@example.com or firstname.lastname@example.org or something in addition to email@example.com, firstname.lastname@example.org, etc. This kind of thing doesn't work if every person in a group has different email (not in a company's domain). But it's a thought.
Anyway read through the documentation Mike posted.