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Connections to the server “p41-imap.mail.me.com” on the default ports timed out.

I can’t send or receive mail using Apple Mail. I can’t access mail via iCloud.com (‘iCloud encountered an error while trying to connect to the server.’).


I have switched Mail off and on in iCloud. Have have signed out of my Apple ID and in again. No result.


I have reinstalled the system software (Catalina).


Anyone have any ideas? I’m running 10.15.7 on an otherwise flawless late-2014 27-inch iMac

iMac

Posted on Jul 3, 2022 1:02 PM

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Posted on Jul 3, 2022 4:00 PM

Remove the VPN. Remove the add-on anti-malware packages; ClamXAV and Objective-See. Given general proximity to the problem area, I'd remove MailButler, and Wipr, and the Privacy Dashboard and Privacy Protection extensions. Remove the Memory Cleaner app. Adobe Flash you've seen, and Silverlight too. And as it tends to mask some controls, I'd disable Screen Time while debugging.

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18 replies
Question marked as Top-ranking reply

Jul 3, 2022 4:00 PM in response to Jack Holland

Remove the VPN. Remove the add-on anti-malware packages; ClamXAV and Objective-See. Given general proximity to the problem area, I'd remove MailButler, and Wipr, and the Privacy Dashboard and Privacy Protection extensions. Remove the Memory Cleaner app. Adobe Flash you've seen, and Silverlight too. And as it tends to mask some controls, I'd disable Screen Time while debugging.

Jul 3, 2022 2:42 PM in response to Jack Holland

Get a complete and current backup, on the off chance that this is a hardware failure happening. Get this backup first, as you might not get as much data back if you try other stuff first (such as running diagnostics) or otherwise delay this backup.


Then run Diagnostics.


Then download and run EtreCheck, and share the report to the clipboard. Then open a new reply here, and press the Additional Text button that looks like a printed page, this will get a big-enough text-input box, and paste the hardware and software configuration report here.

Jul 3, 2022 2:08 PM in response to MrHoffman

Hi Mr.Hoffman


Thanks for this. I had already tried removing the email account – and indeed signing out and back in to my entire iCloud account.


I tried again but I still get the same error message on Mail. And now I can’t see my Desktop anymore (though I have checked the box in System Preferences>Apple ID>iCloud>iCloud Drive> Options>Desktop & Document Folders). After ten minutes and a reboot the desktop has not reloaded, which is worrying.


I have an identical iMac sitting next to the one with the fault which is not experiencing any of these problems. All other mail programs and internet access are fine. The error is therefore presumably on my machine.


All suggestions welcome...

Jul 3, 2022 4:34 PM in response to MrHoffman

Will do. It’s gone midnight local time, so I’ll try all your valuable suggestions tomorrow. (Jack’s rule: never muck about with computers at the limits of your competence at the end of the day.)


Port problem has spread to other Mac (running Mojave for 32-bit apps), so I’m increasingly concerned.


Thanks again for your help; it’s greatly appreciated.

Jul 4, 2022 2:30 PM in response to Jack Holland

Hi Mr. Hoffman


Apologies for the delay in this response. I tried all your suggestions, sadly to no avail. A scan of each iMac’s HD by ClamXav did not spot any viruses, malware, etc. I am now unable to access my email – or anything that requires log-in to my Apple ID – on either of the two Macs. iOS on my M1 iPad is thankfully not affected, and indeed the only way I can send this message.


Having checked the bootable clones on external HDs and Time Machine backups for both machines, I think the most prudent next step is to take my iMac to Apple (assuming they’ll deal with so ancient a device). I’ve tried everything I’m competent to handle, and I’m worried that any deeper tweaking might worsen the problem or complicate the solution.


I had hoped that Apple would release an M1 Pro/Ultra 27-inch iMac for £2500-£3000 back in the spring.  For one aspect of the work I do (using Photoshop to manipulate large RAW images) the 24-inch iMac monitor is too small and the Mini too limited – but at £4000+ the Mac Studio is overpriced and overpowered. Since our small business requires an additional Mac I will probably bite the bullet on the Studio at some point, but I hope my current machine has not reached the end of the road: I have never had a serious issue with it or its slightly younger partner.


I digress. Thank you very much for your prompt and thorough help on this issue. I’ll report Apple’s views when I know them. Your suggestions have also caused me to undertake serious tidying up of redundant software on both my Macs!


All best regards 


Jack

Jul 4, 2022 4:35 PM in response to Jack Holland

I’ll assume you’re connecting using the iCloud access profile, and not using and specifying the POP/IMAP and SMTP settings directly.


Try a different and newly-created login, and add an email account over there. See if this is something (wrong) with your main login.


Also restart the router, and see if there are any router firmware updates available from the router vendor and apply those.


If there’s other gear common to the network path for the Macs, have a look at that, too. If you’re using Wi-Fi, try a wired path.

Jul 5, 2022 6:06 AM in response to MrHoffman

MrHoffman wrote:

I’ll assume you’re connecting using the iCloud access profile, and not using and specifying the POP/IMAP and SMTP settings directly.

I assume so too. I certainly haven't added settings in the way I do for other no-iCloud accounts.

Try a different and newly-created login, and add an email account over there. See if this is something (wrong) with your main login.

Bingo! Works a treat. I don't know what's wrong with my existing iCloud log in, but eventually it refused to accept my password (which I knew to be correct), so I changed the password, but it made no difference to Mail. However setting up a new user account seems to have removed all the issues. Should I try signing out of my iCloud account on my main login then signing back in? (I have already tried this). Is it possible to delete my iCloud account, then re-enter it? (sounds dangerous).


After several days of being plagued with this issue you can imagine how relieved I'd be to fix it!

Also restart the router, and see if there are any router firmware updates available from the router vendor and apply those.

I restarted the router at the beginning of the problem. I haven't checked for firmware updates.

If there’s other gear common to the network path for the Macs, have a look at that, too. If you’re using Wi-Fi, try a wired path.

Both Macs are connected to router via ethernet and wifi.

Jul 5, 2022 8:55 AM in response to Jack Holland

Jack Holland wrote:

Both Macs are connected to router via ethernet and wifi.


If you connect via one oath for tesring, do things work better again?


How many IP router boxes and/or Wi-Fi boxes are involved here?


If more than one router (e.g. one ISP router or router Wi-Fi box, and a second and separate Wi-Fi router box, and with one or more of the Wi-Fi routers not configured as access points), and if IP subnetting is not configured correctly, then you can have IP routing issues.


If you have one router box with both wired and wireless both connected, that usually works fine on any semi-recent box.


Check for router firmware updates, too. I’ve had a few weird cases cleared by vendor firmware updates. And down-revision routers can have latent security issues, which can then introduce all sorts of “fun”.

Jul 5, 2022 9:46 AM in response to MrHoffman

FTTP enters house at a router. This creates the first of of several wifi zones, and is connected to my Mac via ethernet. It’s also connected to a 24-port switch, which from which runs Cat-5 cable to other the Mac and to wifi boosters around in house. This was created for me by a local networking company.


I can certainly try disabling sections of the LAN, but any thoughts on recreating iCloud log-in on main user account? The new user account is running Mail (and all other iCloud services) perfectly!

Jul 5, 2022 11:44 AM in response to Jack Holland

Ah, that config sounds familiar, and usually working around here with an ONT on the outside wall, or with fiber to an ISP router.


You’ll likely want all that APs and not Wi-Fi routers and “zones”, too.


I’m wondering here about whether the issue is with IP network routing, and that can provide different results depending on the path, and a new login can also provide different IP path defaults. Subnetting is usually necessary when there are multiple network paths, when there’s a DMZ (outside the discussion here), and with cases where more than one router is involved.


If you’re wired all the way to the ISP router or ONT (ignoring any unmanaged or not-hostilely--managed switches and with exactly one ISP router or ONT in the path), then that should all be one subnet, which would put this into your network settings.


Shut off Wi-Fi on the Mac and see if you get mail connectivity established, if wired through to the fiber and with exactly one router in the path between your Mac and the fiber; with just the ISP router or ONT box.


PS: Cat 5 is kinda sketchy for gigabit, though (officially) workable.


Jul 5, 2022 1:12 PM in response to MrHoffman

Thanks. I tried switch off wifi, but the problem persists.


I also made another rookie error in failing to delete the new user profile correctly, meaning my HD is now full. I tried booting from the clone and finding and emptying the .Trash file but that didn’t work.


For my own sanity I’m booking the Mac in with my local Apple dealer tomorrow.


Thanks for all your hep


Jack

Connections to the server “p41-imap.mail.me.com” on the default ports timed out.

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