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Here's my story:
I got tired of looking up people's email addresses when I needed to send an email to "all bishops" or "all bishoprics" or "ward mission leaders and elders quorum presidents" or "all HPGL secretaries".
So, I manually created email aliases, alias@mystake.org . All you had to do was send an email to "bishops@mystake.org" or "hpgls@mystake.org" and it would send an email to those people.
This was fine, until I realized how often callings/responsibilities change...
So, I did what anyone with a little time and scripting knowledge would do, I automated it!
I signed up for mailgun (once) and I download a CSV file from MLS (weekly). I then wrote a program to analyze the CSV and make REST web calls to mailgun.com to update the email aliases.
"THIS IS AWESOME" I thought.
Until the email bounces started happening... I started sending the first few emails and AOL blocked emails coming from mystake.org. I asked their postmaster to unblock me and I got no response.
Then comcast blocked me, I submitted a support request to comcast and they unblocked the mailgun IP and emails started going to comcast again.
I opened a ticket with mailgun and they changed the sending IP in hopes that AOL would unblock my outbound emails.
Unfortunately, comcast didn't know of the new IP so comcast started blocking again and AOL still blocks the new IP address.
Meanwhile, other leaders in the stake have started using the aliases (they're WAY easy to use!) so I see in the logs how their messages go out to other people, but anyone on the list that has an AOL account doesn't get the messages.
Then today, gmail started blocking me.
"This is LUDICROUS!" I thought. I'm sending emails reminding people of meetings, asking for approvals, and coordinating stake conference... and everything gets marked as spam. I've verified domainkeys is working and set everything up how the instructions said to (mailgun's instructions).
Instead of spending time manually updating aliases, I've simply shifted my time to contacting domain postmasters and watching logs to make sure things are being delivered.
I'm thinking about dropping this whole thing... which is too bad because it was really awesome while it worked.
Perhaps I keep the automation, but when people email alias@mystake.org they get an automated reply with all the email addresses for that alias. I think that this is where I'll end up... simply because it gets me OUT of the business of ensuring mail delivery and instead puts the onus back on the email sender.
It is also easy to automate... I'll just have to keep taking a CSV export of MLS until I come up with something else

Has anyone had better luck with this sort of thing than me?
Thanks~!