SMTP + SSL troubles

I see a smattering of discussion in the past about this, but I've run head long into it. It's not a show stopper, but I'm curious: I have domain hosting with tchmachines. I've set up various email accounts there to support various home automation tasks and such, and recently tried to shift to all-ssl incoming and outgoing emails from the server. TCHmachines asks for non-secure SMTP domain customers connect to "mail.(your domain name).com" on port 26. They ask those wishing to use SSL/TLS for SMTP to connect to a specific server in their array like "foo.tchmachines.com" on port 465.

SMTP to the non-SSL side works great. SMTP pointed at the specific machine they ask me to with SSL/TLS checked to port 465 never connects, times out, and tries again every 10 minutes forever. Trying to be tricky and UNchecking SSL/TLS whilst leaving the email preference set to the specific hosting machine as they require on port 465 generates a very helpful log entry "no response from SMTP email server -- try enabling SSL on Email tab in the Preferences Dialog"

When set up correctly with the target SMTP server's qualified name, port 465, and SSL/TLS checked, the status line in the main window never progresses beyond "Email send; connecting..." then times out and tries again in 10 minutes. It's working from my indigo machine in other apps (notably SecuritySpy...), I've stopped/started/restarted the server and the machine, and I'm running 7.2.

Any thoughts? is SSL on port 465 just broken for now?

EDIT: Fwiw, receiving email following the domain host's setup (pop3 server set to the direct machine rather than the domain alias) on port 995 works great and pulls down email with no issues.

TIA

PS - is there a way to STOP an endlessly retrying every 10 minutes email send once it's started other than fiddling with settings in the email preferences tab and hoping for the "email stopped" entry to come along?

The email library in the Indigo server is old and buggy. You're really better off switching over to the BetterEmail plugin for sending email.

PS - is there a way to STOP an endlessly retrying every 10 minutes email send once it's started other than fiddling with settings in the email preferences tab and hoping for the "email stopped" entry to come along?

I believe that restarting the Indigo server will clear the email cache.

ugh. copy that and copy that, and thank you.

So Indigo after all these years and updates now needs someone else's plugin work to make it capable of EMAIL bug-free? Oh good gravy.

Email:
Indigo 7.4, BetterEmail 7.2.7, trying to send notifications. Had email working fine with just indigo until I changed email, now I can't get Gmail or Yahoo to work from Indigo, both work fine outside the program for sending & receiving, ( this has been going on for a while now, before I did program updates ).
I get ( Better Email Error Better Email sending: SMTP server connection error: (535, '5.7.0 (#AUTH005) Too many bad auth attempts.')

So, hope someone could maybe shed some light as to what I may have done. Thanks

Email:
Indigo 7.4, BetterEmail 7.2.7, trying to send notifications. Had email working fine with just indigo until I changed email, now I can't get Gmail or Yahoo to work from Indigo, both work fine outside the program for sending & receiving, ( this has been going on for a while now, before I did program updates ).
I get (

Code: Select all

Better Email Error              Better Email sending: SMTP server connection error: (535, '5.7.0 (#AUTH005) Too many bad auth attempts.'

So, hope someone could maybe shed some light as to what I may have done. Thanks

That looks self-explanatory. You have the wrong password and it's locking you out. What SMTP server is this trying to connect to?

Gmail you need to turn on "less secure clients" or something like that. I don't know anything about Yahoo mail.

Google will likely be the option Joe mentions about allowing non-secure clients.

https://support.google.com/cloudidentit ... 0879?hl=en


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I have an extremely frustrating ongoing relationship between both Indigo email approaches and gmail (and various other mail services).

There seems to be a repeating cycle of authorisation changes breaking things.

Google will likely be the option Joe mentions about allowing non-secure clients.

https://support.google.com/cloudidentit ... 0879?hl=en

I guess the google issue begs the question of why Indigo doesn't support the more secure architecture Google etc prefer.


I love the way Security Spy offers its own mail server [only for SS messages of course], it is a rock solid approach.

I guess the google issue begs the question of why Indigo doesn't support the more secure architecture Google etc prefer.

Because it requires OAuth and it's a royal pain to implement. Which is why I haven't done it. And the email framework that Indigo uses is even older and more decrepit, which is why they recommend the plugin on occasion.

Seriously, almost any other free email provider is easier to work with than Gmail. So why use Gmail unless you're using that account for Google Docs or something else integrated with email. iCloud works pretty easy with their app-specific passwords. GMX works just fine with no messing around.

Good advice then - I've tried several other providers (AU-providers) but with similar issues to Google.

I'll definitely try GMX, thanks for the tip.

I find managing multiple iCloud accounts can also be a trap if not careful.

Only downside to GMX is that it doesn't seem to support IDLE mode very well. Maybe it's gotten better.

Personally, I stopped using any of the "free" providers for my primary account. I use Rackspace, for which I pay $12/mo for 5 mailboxes (accounts). Rock solid dependable, and I know they're not trolling my emails. I have iCloud and Gmail accounts (several of each), but only use them as backups or dedicated to HA purposes or testing. But that's just me.

Understood ..I also don't use like the idea of Gmail for a primary account.
I prefer to use as service hosted in a jurisdiction with strong privacy controls (probably not US ).
But for automation projects....just want something that works- preferably just recycling one of the many free accounts I get with my ISPs, or one of the free services!!

[jay (support)]

+1 on the OAuth comment - it is the most (overly) complicated, designed-by-committee standard I've ever had the displeasure of having to deal with (and I once, long ago, worked for a government contractor).

OAuth is super overkill when used in this kind of hands-free automated way really. I agree that finding a different email provider for automated emails it really the best way to go.