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wegster

macrumors 6502a
Original poster
Nov 1, 2006
642
298
So, this has been...frustrating. I have an 'OG' gmail account from invite-only days, and of course, will all the corresponding spam that goes with it, some crazy 100K+ unread mails in it. Some of which were my own fault, making the mistake of signing various petitions, letting online retailers etc. add me to subscriptions, etc. - but it became time to 'take my email back.'

As virtually every reasonably sane combination of gmail username was taken to add second/third etc. email accounts - enter gmail aliases, which allow you to add +<something> to your base email address, set a flag to 'treat as alias,' and it effectively becomes a new email. I've added labels and gmail-side filtering for each +<something> so in effect, I now have multiple inboxes. This took a little bit to sort, but works fine on my Mac, and I've dragged each of the 'labels' (e.g. email+shopping@gmail.com winds up in my Shopping folder) into Favorites on my MBP, so it works pretty well other than Google datamining my emails (have disabled all 'smart' features, at least), and can always add more dynamically.

Note - once set up properly, you can also send AS the e.g. email+shopping@gmail.com address, at least on the MBP/macos...without issues.

On to the pain. I've sort of had this working on the iPad, but .. .not quite.
1. On the iPad, I can see the 'labels'(folders for e.g. Shopping), but there's no favorites or way to drag them up higher. Not thrilled, but can live with this.
2. Most importantly, I can't seem to reliably reply to mails using one of the gmail aliases. On the iPad, I have the gmail account set up as IMAP versus a 'google' account on the MBP, which seems to have been the common recommendation for setup on iPad or IOS.

The latest error set is one of two:
1. When trying to reply from one of the alias accounts: :The connection to the outgoing server smtp.google.com failed. Additional Outgoing Mail Servers can be configured for Mail accounts in Settings > Accounts & Passwords.
2. When sending a new mail from an alias: "Cannot send Mail. The server rejected one or more of the recipient's addresses. The message has been place int your outbox.'

So that pair is rather confusing - if indeed I can't reach smtp.google.com (case #1), then how exactly is the server rejecting anything at all? (#2)?

Of course, actual server settings are inconsistent between macOS and iPadOS/IOS, and nothing I've seen seems to clarify with respect to current iPadOS (in the event anything's actually changed), although I've seen numerous people having problems with gmail aliases over time.

I AM still trying to also keep my google calendar, so technically have one 'gmail' account for everything but mail as a 'Google' account, and then IMAP for Mail only.

Has anyone gotten this working 100% and can share some tips? A quirk in iPadOS seems to have some issues and LONG delays when playing around with mail server settings/making changes - making this even more frustrating.
 

wegster

macrumors 6502a
Original poster
Nov 1, 2006
642
298
Ok, and...I think it's sorted. I can't say at this point what did it - I deleted both my 'google' account (calendar, contacts) and IMAP google accounts completely, re-created IMAP first, then added in the aliases, then added Calendar as another account as a 'Google' account, and it's sorted.

Probably got wrapped around the wheel a bit after going through and changing every server setting etc.
 

AutomaticApple

Suspended
Nov 28, 2018
7,401
3,378
Massachusetts
Ok, and...I think it's sorted. I can't say at this point what did it - I deleted both my 'google' account (calendar, contacts) and IMAP google accounts completely, re-created IMAP first, then added in the aliases, then added Calendar as another account as a 'Google' account, and it's sorted.

Probably got wrapped around the wheel a bit after going through and changing every server setting etc.
Well, we're glad that you were able to solve the problem on your own. :)
 
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