Ever since moving to the island, I’ve had trouble with emails disappearing into the void. On the mainland, I had a nice, stable static IP address at my home with a good email reputation (not suspected of sending spam). I haven’t been able to get my local ISP to even answer my question if static IP addresses are even available. I truly don’t think the support staff even know what a static IP is, and when I escalate to engineering I never hear back.

After I moved, I used some VPN trickery to use a VPS for my mailserver address while keeping the actual server local. It all seemed to work, except that some providers didn’t seem to like my VPS IP address. None, I repeat none actually bounced any email from me, but did the horrible thing of accepting and acknowledging delivery of the mail while hiding it from the recipient as spam and deleting it without notifying the recipient. Disgusting. That’s like the controlling mother who hides the letters from her daughter’s long-lost love leaving the daughter to believe her sweetheart just never answered her heartfelt notes. Naughty Google.

I switched to Fastmail for outgoing mail, and everything seemed to work. Almost. I still had the occasional lost email, and couldn’t figure out why.

A few days ago, it occurred to me that it might have something to do with multiple email addresses. I have many, many email addresses (I’ve been in this field of poppies a loooong time). Let’s say, for example, that I have a twoprops@example.com email address and a 2props@example.com email address. Different addresses, but both are on the exact same account (actually @twoprops.net but I don’t want to encourage more spam by writing those addresses out in full). I use Thunderbird for my desktop email client, and all seemed to be well until I realized that sending mail from twoprops@ went through my Fastmail server, but sending from 2props@ even though it’s the same account caused Thunderbird to send my email directly from my local, dynamic IP address. Since that’s a dynamic IP and reverse delegation (it’s a DNS thing) shows it to be a residential line, a lot of email providers don’t like it. I triple checked that Thunderbird had the proper (Fastmail) outgoing server, but it still refused to use it. I searched settings, but came up with nothing. As it turns out, one must:

  1. click on the Edit menu
  2. choose “Account Settings”
  3. go to the very bottom, where you’ll note the proper Outgoing Server is configured but then…
  4. click on the “Manage Identities…” button
  5. in the popup window, click the domain that’s intermittently failing (eg. 2props@example.com)
  6. click the “Edit…” button
  7. scroll to the bottom
  8. click the “Edit outgoing server…” button
  9. enter all the configuration information for your outgoing server, just as you’ve already done for this same account where there is no reference to it being “per identity”
  10. click OK
  11. click Close
  12. close the “Account Settings” window

In other words, all you have to do is realize that configuring the “default” outgoing mail server and the account outgoing mail server will still result in any secondary identities using the wrong server, and then follow this simple, hidden, twelve-step process to stop Thunderbird from defaulting to what, for almost all residential internet users, will be a horrible choice for outgoing mail.

Sheesh.

—2p

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