Using Indigo Mail

I am using Indigo 7.0 .4. Everything works very well, it does everything I need, upgrading would require new Mac, so there's really no reason to upgrade.

I used to use Gmail as the configured Indigo "Email Sending" server configured in Indigo email preferences. This worked until May or so of this year when Google changed things.

I am trying to set up my iCloud account in Indigo-Preferences-Email, but I can't get it to work.

On the Apple Computer, their default Mail program uses the same iCloud account. It can send email successfully. I would like to use the same account in Indigo.

I have indigo-Preferences-Email configured:
SMTP Server: smtp.mail me.com
SMTP Server Port: 587 Use SSL (TLS) checked
SMTP User Name: bfschler@icloud.com (my iCloud account)
SMTP Password: *** (my Apple ID password)
Reply to Email Address: bfschler@icloud.com

Thanks for any help.
Barry.

You need to use an app-specific password for non-Apple email clients.

https://support.apple.com/en-us/HT204397

Thanks very much!

Thanks, but unfortunately that did not do the trick.

My Indigo Preferences-Email configuration looks like:
SMTP Server: smtp.mail me.com
SMTP Server Port: 587 Use SSL (TLS) checked
SMTP User Name: bfschler@icloud.com (my iCloud account)
SMTP Password: *** (generated App Specific Password)
Reply to Email Address: bfschler@icloud.com

I've seen different things doing Google searches where it would say "if that doesn't work try port 465, or if it still doesn't work …"

Any other suggestions?

Thanks,
Barry.

Try StartTLS instead of SSL.

Still no luck using my iCloud mail account via Indigo mail. I've tried everything I can think of. I've searched Google and tried the recommendations.

The errors I receive in the Indigo log are:
Error email send connection failed
Error mail re-send scheduled in 10 minutes

I've attached a screenshot of the Indigo-References-Email dialog box from Indigo. I should mention again that I'm using Indigo 7.0 .4 since it works great, does everything I need, and it would require me to upgrade my Mac if I upgraded to the newest version.

I used to use Gmail, but they now require a new authorization method.

Things I've tried:
I've tried using ports 587, 465, and 25.
I've tried having both SSL checked and unchecked (The way the dialog box shows I believe unchecked will cause TLS to be used)
I've tried using my full email address bfschler@icloud.com and just the name portion "bfschler".
The password I'm using is the App Specific Password I generated on the Apple site after logging in with my Apple ID. I've set up two factor authentication.

I can send mail using the built-in Mac email program and the mail shows up as coming from bfschler@icloud.com

Any ideas I greatly appreciated.

Barry.

Since you're on Indigo 7, try using the Better Email plugin instead of the built-in Email sender. It works better, which is why Indigo 2021 and later use it for email (renamed to Email+).

Thanks for recommending Better Email. I will give it a try.

I have looked briefly at the documentation. Is it true that Better Email still uses the Indigo email transport layer, but adds more upper level features?

From the errors I'm receiving,
Error email send connection failed
Error mail re-send scheduled in 10 minutes,
my guess is that I'm having problems at the transport level.

The plot thickens –
I tried configuring Indigo Email send for my web host email account. I've connected to this host from dozens of clients on Windows, Mac, Android, IOS, microcontrollers, …
In indigo I get the same errors, although the built-in Mac email client sends and receives properly.

I connected Indigo Email to Google Gmail for years without a problem. Only when Google started requiring OAuth2 was their problem. Since I'm using an older version of Indigo, I can't really expect support for OAuth2..

Can anyone recommend a free email server for very tiny traffic? I send about a dozen emails per month from Indigo.

Better Email uses a totally different (pure Python) email library. The built-in Indigo email uses an old C/C++ library, which is really old.

I use GMX for email testing, it's free and works reasonably well.

I know iCloud works with Better Email, but you do need to use an app-specific password.

Thanks. I will definitely give Better Email a try.

Thanks. Better Email works great!

Installation and configuration were easy. I closely followed the documentation.

I had to change SSL to Start TLS for my iCloud account.

I had to change SSL to Start TLS for my iCloud account.

Yeah, that's a recent change. Docs are out of date, but the only users for that plugin are running Indigo 7 or earlier. Indigo 2021 and later use the included Email+ plugin, which is based on Better Email.