Is this a Mac Mail problem, or my host server's issue?

Dvanetc wrote:

Well, it seems this issue has something to do with Catalina and my my old MBP. An Apple Senior Advisor went over all the steps I've gone though and finally said there was nothing else to be done... they can't keep supporting older software beyond a certain point, and it seems I've reached it! I downloaded Air Mail from the App Store, and in 5 minutes had it set up and sending emails from both of my accounts. (!) So until I bite the bullet for a new Mac, I'll have to pay $2.99 a month for a subscription to Air Mail. At least it's well-designed and seems to work well. I'm just used to free Apple Mail... but now that I think about it, Apple Mail has kind of been a problematic email client for years! Maybe I'll like Air Mail enough to keep it.

you can submit your Apple Feedback hhttp://www.apple.com/feedback

Now it should be "It might work..."

I've had exactly the same problem (with a mail account hosted through my domain at Hostmonster). Receiving is fine. If I send mail through Apple Mail, it appears to go out normally ... but then vanishes. No bouncebacks; no deliveries to spam folders. Just gone. Hostmonster can find nothing wrong with my account. Also, web mail works fine.

Two other oddities point to it being a problem with the Apple Mail app:

1) I installed Microsoft Outlook and set up the same IMAP account. Outlook sends messages with no problem from the same computer. So, if I send a message through Apple Mail, it vanishes. If I send a message to the same address through Outlook -- no problem. (I hate the UI of Outlook, so as a workaround I'm reading incoming messages in Apple Mail...then replying through Outlook!)

2) I have 2 iMacs (in 2 different locations). Upgrading one of them from Catalina to Big Sur seems to have fixed the problem. But the other one is too old to upgrade to Big Sur, so I'm stuck on Catalina.

All in all, everything points to a problem with Apple Mail.

Dvanetc wrote:

Thanks for the response Bob, I am sending from my usual home office wifi... Bluehost tech support has not mentioned anything like a relay... (I've had 3 phone tech support sessions with them. They seem to think all is well on their end, due to the success of sending with webmail.) I have had issues like this in the past (been with Bluehost many years) where their servers were hacked by bulk spammers and my email suffered by association. (Or so I've understood.) But they don't seem to think so this time and they've been unable to solve my problem. Bluehost did send me a notice about my account being hacked a few days before this all started. They recommended that I change all my account and email passwords, which I did. Again, connection doctor is showing all is connected, so I don't think my messing with passwords did anything...

You can check if your IP address or domain name is on a blocklists—

to easily see your IP... https://www.whatismyip.com/

https://check.spamhaus.org/

Dvanetc

It sounds like we've followed the same path, and have come to similar conclusions. Apple Mail works fine on my iPad, iPhone, and an iMac that I was able to update to Big Sur. But on my older iMac and old MacBook--which can't go beyond Catalina--Apple Mail still won't send.

As an alternative to paying for email, I've been using Microsoft Outlook (which came as part of the package with my Office subscription; I'd just never used it). I'm currently using Apple Mail to read incoming, since I like it's interface, and Outlook to reply -- which is weird.

I've also tried the free Spark, which has a cleaner interface than Outlook (it's in the the app store). And I'm going to check out the open source Mailspring, which I've heard good things about and apparently has a robust free version.

Has it ever worked under Catalina? Maybe one of the recent security updates caused the issue.

I would imagine many people use Blueshost, but perhaps not. Seems like there would have been a lot more posts about it if had affected Catalina from the outset.

Any idea what they are using for their email server?

Have you turned off the Automatically manage server connection in Mail? I have two accounts through my ISP that I set up in Mail and had a lot of trouble getting it to accept the different username/password combinations without turning off Automatic connection management. I see those instructions listed for Yosemite, but I know I was disabling it well after Yosemite. It is currently set on my account in Big Sur, but it isn't crushing the settings, either.

My experience was the same. Mail worked fine until I installed the latest security release upgrades. I actually sent an email with no problem, then restarted with the upgrade, and then lost the ability to send. This happened on 2 different computers. So it would seem that the latest upgrade "broke" Mail.

I can confirm however that several other email applications I've downloaded seem to work fine. I'm trying several now to decide which I prefer.

One possibility is that you are trying to relay email through Bluehost when connected to some other network. Most email/hosting providers do not allow relaying of email.