Mac Mail showing connection timed out but getting emails

Just moved my DNS from Namecheap to Cloudflare about 2 hours ago.

All seems great but Mac Mail is showing the triangle exclamation point with:
Connections to the server “wednesdaysinmhd-com” on the default ports timed out.

If I click on Edit and change the ports as recommended in cPanel (993 in; 465 for SMTP), I get a long wait then a message that the username or password could not be verified.

Currently outgoing emails from that account are stuck in Outbox but getting incoming email.

I tried adding an MX record for wednesdaysinmhd-com as mail-wednesdaysinmhd-com

Also later tried adding A records for mail to my server IP. Also did same for smtp.

Cloudflare had created a CNAME for mail which I deleted before creating the same as an A record.

I’m not sure what else to try/do at this point. Note I had to change URLs to use - since I exceeded the 4 links per post limit for newbies.


Are your records proxied? If they are, and you are using them to host a mailserver, they need to be set to DNS Only :grey: since the proxy only passes HTTP & HTTPS traffic.

Thanks for the quick reply!

All records need to by DNS Only? I changed the mail related A records but that hasn’t made a difference

Had to disable my site on Cloudflare

Tried making the MX record be root and point to

Set up an A record for mail to point to my IP

Every time I set those accounts in Mac Mail with the settings of using the mail server as above (which is what is instructed in my cPanel), the account would seem to work for a second and then showed as disabled in Mac Mail.

Can only get mail to connect if I disable my site on Cloudflare.

Meanwhile I have a smaller site on the same server with a different Cloudflare account and that one seems to be working fine. All records are similar. No clue how to fix this.

On Cloudflare, the A record for mail needs to be unproxied.

In the mail client settings, you must use the server name Ensure (by unchecking “Automatically manage connection settings”) that IMAP is using port 993 and that TLS is enabled, and that SMTP is using 587 with TLS enabled. is answering on both of those ports, so it should work, as long as you’re not trying to connect to the root domain.

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Using TCP 465 with SSL for SMTP is also a good option, when available, since it uses implicit TLS.

Thank i40West

So I tried that with all those settings except had SMTP as 465 which is what my host recommends

When I did that in Mac Mail, All the settings saved but then the account went into disabled mode. If I tried to enable it, my password was empty on the IMAP section and the server had reverted to

I also tried making an A record for smtp at one point which didn’t do anything helpful.

I currently turned off Proxy for everything but have Cloudflare otherwise enabled and just doing DNS and it seems to be working fine. Not ideal but not sure how to fix this otherwise.

Here is what I have now with the server IP blacked out and three entries for Amazon SES DINK or something like that

Update: Even with the above settings, in Mac Mail, when I try to change host name from to, I get username/password and connection errors. These errors only go away if I check Automatically manage connection settings and keep server without the ‘mail’

So if Mac Mail insists on using IMAP via wednesdaysinmhd-com, how do I then change the MX and correlating A records?

Also, SMTP still has the hostname as mail-wednesdaysinmhd-com (dashes instead of periods as forum blocking me using too many links)

Port 465 was un-deprecated not long ago, so that’s fine too. Your mail server supports it.

I have no idea why you would get an error on the mail hostname but not the root domain because (right now) they both point to exactly the same place. But email is never going to work on the root domain if Cloudflare is enabled on it. Email should always be set up on a host, not the root domain, because of exactly that kind of conflict.

But I don’t know how to fix the error; it’s probably between the mail program and the server at this point. There’s no reason I can think of that the same password wouldn’t work when you set it to

Thanks. At least I’m not crazy for thinking this makes no sense…

Opened ticket with host so we’ll see what they say

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