Apple Mail app and Yahoo IMAP

[BKDad]

Recently I've been having some beach balling with Mail and deleting messages has been taking too long.

Setup summary:

Mac Studio using Sonoma 14.6.1
Two Mail accounts. One with iCloud via IMAP and one with a Yahoo account that was originally run by ATT, also via IMAP.

The iCloud account normally runs very well. The Yahoo one is, ahh, inconsistent. This shows when I delete messages in the Yahoo based account - it often takes many seconds while the message is being moved.

I've reset the Mail junk folder, started Mail in Safe mode, started the Mac in Safe mode and started Mail in Safe mode, cleaned the DNS cache, and rebuilt the mailboxes. These have had some benefit, but haven't solved the problem.

EtreCheck doesn't report anything bad, for whatever that is worth.

I had been using SMTP port 587 for the Yahoo account. Many sources online (Danger, Will Robinson!) suggest that this is the preferred port. But, when I switch to port 465, things seem to work much better with Mail on my Mac.

So... Is there a reason why port 465 might really be less desirable to use? Security? Or, is there anther solution to this problem?

Thanks!

 

[Fishrrman]

"I had been using SMTP port 587 for the Yahoo account. Many sources online (Danger, Will Robinson!) suggest that this is the preferred port. But, when I switch to port 465, things seem to work much better with Mail on my Mac."

Fishrrman's "Mac Rule Number 2":
Use what works for you. Don't waste your time trying to use what doesn't.

If port 465 works better, why not "just use it"?

Personal experience:
I don't use iCloud and I don't own a smartphone (one of the few people in this world who doesn't, I gather).

But... I, too, use a legacy email address from the "att days" (in this state, before they sold out) that is now hosted on the yahoo servers.

But over the years, there have been days (sometimes several in a row) where trying to connect to the yahoo servers has been... let's just say it was "a pain".

Seems like a number of ISPs have "off-loaded" their email to the yahoo system over the years.
And MANY users have had connection problems.

Only two days ago, I spent a few hours at a friends, who uses (like me) an "att legacy email address" again through yahoo. He kept getting "!" notices that the connection wouldn't "make".

We finally got it resolved (at least for the moment). For some reason (he's with comcast cable now), the yahoo servers kept thinking his comcast email address was spam, and it looks like yahoo kept "cutting the connection".

I just happened to discover this by chance, by going to the yahoo WEB-BASED email (directly on their server, without using Mail.app), and then marking incoming email from comcast as "NOT spam". Then it seemed to work.

Easy, eh...?

Again, I'd just use "whatever seems to be working for you", and try not to worry about it until things break again. As they probably will ....

 

[BKDad]

"I had been using SMTP port 587 for the Yahoo account. Many sources online (Danger, Will Robinson!) suggest that this is the preferred port. But, when I switch to port 465, things seem to work much better with Mail on my Mac."

Fishrrman's "Mac Rule Number 2":
Use what works for you. Don't waste your time trying to use what doesn't.

If port 465 works better, why not "just use it"?

Personal experience:
I don't use iCloud and I don't own a smartphone (one of the few people in this world who doesn't, I gather).

But... I, too, use a legacy email address from the "att days" (in this state, before they sold out) that is now hosted on the yahoo servers.

But over the years, there have been days (sometimes several in a row) where trying to connect to the yahoo servers has been... let's just say it was "a pain".

Seems like a number of ISPs have "off-loaded" their email to the yahoo system over the years.
And MANY users have had connection problems.

Only two days ago, I spent a few hours at a friends, who uses (like me) an "att legacy email address" again through yahoo. He kept getting "!" notices that the connection wouldn't "make".

We finally got it resolved (at least for the moment). For some reason (he's with comcast cable now), the yahoo servers kept thinking his comcast email address was spam, and it looks like yahoo kept "cutting the connection".

I just happened to discover this by chance, by going to the yahoo WEB-BASED email (directly on their server, without using Mail.app), and then marking incoming email from comcast as "NOT spam". Then it seemed to work.

Easy, eh...?

Again, I'd just use "whatever seems to be working for you", and try not to worry about it until things break again. As they probably will ....

Thanks.

Yeah, you'd think that email would get fixed by now. It's one of the oldest - maybe *the* oldest * - internet functions in existence. But, I guess not. Probably it's not cool enough to devote resources to.

My only concern about port 465 is that a lot of online experts say that it is less secure, even though it uses SSL/TLS encryption. Who knows? Pick an expert you like, I suppose.

I'm sticking with 465 for now.

 

[bob_zz123]

Ultimately a port is a bit like a phone line, you can have any type of conversation down it (regardless of the port number) as long as both ends understand each other. We have conventions that specific applications use specific ports but there's not actually any type of technical limitation.

Port 465 is used for Impicit TLS, the convention is that connections on port 465 are meant to be always encrypted.

Port 587 is used for STARTTLS, with this the convention is that the conversation starts as unencrypted but clients can request the conversation "upgrade" to TLS if both ends of the connection support it. A benefit of this approach is that it is backwards-compatible.

Ultimately I'd go with what Fishrrman said, just use one that works.

 

[BKDad]

Good explanation. Seems like both are encrypted, it's just a matter of which encryption technique is used.

Thanks!

BTW, does this suggest that connections to port 587 are always negotiated, while connections to port 465 are always expected to be encrypted with TLS? That might mean that the negotiation phase between Yahoo and Apple Mail is kind of messed up. I'd guess that each time I try to Delete an email in the Yahoo server. it's taken as a new connection since I'm trying to move a message. If this negotiation is a struggle, something less desirable probably happens, like a time-out of some kind. That make sense?

 

[BKDad]

Weekend update:

So far, so good with Port 465.

I also learned that deleting messages by just hitting Delete over and over for each file I want to move takes a lot longer than just selecting them all as a group and hitting delete once. It seems like when you do the delete as a group, it's a single transaction that Yahoo accepts faster than each one individually with its own transaction.

It also goes faster to do one account at a time - in my case, one is iCloud based and the other is an offloaded former ATT account from one of the companies they acquired years ago that's run on a Yahoo server.