In recent days I have sent from Apple Mail app (os sequoia) to family on gmail and vice versa. Neither of us is receiving the emails nor any notice that the sending failed. They just seem to go into the ether.
I searched online, time limited to the last week and month, and didn’t find any pages discussing such an issue (maybe bad keyword choices).
I recall some similar issue months ago in one direction, mails from various OSes and apps disappearing into Google with no failure message to sender and recipient not receiving the email. That turned out to be something with Gmail looking for some kind of security indicator in the header that needed to be set on senders side. I don’t recall reading about Apple also ‘disappearing’ incoming Gmail lately.
Has anyone heard of this in the last week? did Google make some other change in its expectations for incoming email?
Meantime I’ll suggest family use their rarely used/checked Apple email.
I sent test mails from my gmail to my icloud and from my (little-used) icloud to my gmail on a Mac running Sonora and everything went through. Could you be having a spam-filter problem? Those can be rather quirky and very hard to track down.
Thanks Mr. Hecht, from my side, I do check the mail marked spam several times a day and didn’t find the expected email there. Perhaps Apple deleted it before the inbox although I have never over decades marked the sender’s address/mail as spam.
From me outwards, hard to say as we are not colocated and she is very busy and not particularly interested in tech details.
Must be unique to us if there’s not a known situation out there.
I recently sent email from my own server to a gmail address with a bcc to my wife’s icloud address. It was a completely innocuous email (asking about worms for my composter). Apple bounced the mail with a link that sent me to a page that was all about how to do bulk mailing to icloud. I sent the exact same mail but with my wife’s icloud address in the cc: field instead of bcc: and the message went through.
Senders don’t always see bounce messages, because they often get filtered out as spam which really makes troubleshooting difficult.
With Google? I wouldn’t be surprised if they downrank search results that point out problems with gmail.
I have had some problems lately with tech-savvy recipients saying they never received email that Google reports as delivered to their mailbox. I had attributed it to things getting sent to the user’s spambox, which Google periodically empties without notice (I think this is only one small notch above the reprehensible practice of silently deleting email that you’ve reported to the sender as accepted). I’m seeing more complaints about missing gmail, though, and I’m beginning to wonder if Google isn’t having internal delivery problems. Gmail has always been a moving target and sometimes, in their zeal to stay ahead of spammers, they make friendly-fire victims of their users.
Even though I am proud of my painstakingly developed Boolean and search engine query skills, I really like the generative AI search engine perplexity.ai .If a traditional search site is going to be complicated to use for something (say, because I only have a vague recollection of something I’m looking for or I’m not sure of the exact wording I need to use), the conversational language prompts at Perplexity make searching easier and quicker. Plus I appreciate how Perplexity cites its sources unlike most other genAI’s.
Thanks for the reply and testing Mr. Risley,
Nope, haven’t used that for years.
Will have to try alternates and through Signal point out that i sent something to a nonstandard address. Might work short term til she is back here at base and I can poke around her Mac.
Seems it’s bigger than thought. Over the last 10-14 days many family and business emails at a wide range of domains indicate they have not rec’d my emails at all.
My first step to test was sending from an iCloud address to 4 different email addresses and an Apple address.
All show arriving the same minute as sent.
So maybe it was a temporary glitch at Apple or something but it makes me wonder for future how I can know if emails were ‘disappeared’ by Apple or somewhere else along the way, other than by not getting a response from recipients.
Apple email has been very reliable for… decades!
Since I get no indication that an email was not properly delivered, is there some other technique to use generally? Is there something in the headers of outgoing mail I can check somehow, set a rule for etc?
Meanwhile I’m going through email of the last few weeks and calling by phone or texting those who haven’t replied.
Lots of our family don’t pay attention to or regularly use email or Messages anymore, so their non-responses are expected, but businesses generally do respond even if automated.
I use VPN products from PIA (Sequioa Mac) and OpenVPN (Sierra Mac) if that could be part of the issue…
Grateful for any ideas.
Any technique that can reliably be used to verify successful delivery will immediately be embraced and abused by spammers. Email systems will then implement countermeasures. Think read receipts (now ignored by most email systems) or image bugs (leading to clients that don’t load images by default, plus more sophisticated techniques such as Apple’s email privacy settings).
About all you can realistically do is either ask people to reply confirming receipt or follow up out-of-band (phone call or text message)
Mr. Risley, thanks again for the info and perspective.
I already spent a few hours going through sent emails and checking with recipients by phone, SMS etc. and haven’t yet found the date when this all seems to have started.
As noted, I’ve had really good success with Apple email for decades so having multiple outgoing messages disappear into the ether over many days is frustrating and distressing.
Will post again if/when I discover something new in case the info is helpful to another T-Talker.
Is everything getting blocked, or is some getting through? If so, what is getting through? How carefully have you checked your outgoing for spam signals or for a malware infestation? Have you set up your server to forward any of your mail automatically? Have you tried Apple Support?
Mr. Hecht, thanks for the questions/ideas!
- I’m still analyzing what went through and what didn’t-some I have contacted on this issue thru other channels have reacted with suspicion that my follow up is genuine, complicating the problem
- I don’t know what you mean about ‘spam signals’ or ‘malware infestation’. I’m a ‘normal person’ writing ‘normal email’ as I have for decades to friends, family, businesses, no change in tone or anything
- My ‘server’, so far as I understand it, is Apple. I’m not sure how to ‘forward’ outgoing email, will have to research that
- Apple Support is a joke, I gave up on useful help there long ago, along with its ‘communities’ or what it’s called. I asked here as Tidbits Talkers tend to provide better support!
By spam signals I meant keywords that spam filters consider signs that the email is spam, such as a scammy offer for very cheap’ copies of commercial software. Many spam filters count how many suspicious words are in incoming mail to identify what might be spam.
A “Malware infestation” is something that attaches malware to your email, perhaps as an attachment.
I have had reasonably good results with Apple Support, including helping me transfer my email service to a new server. They don’t know it all, but they usually know more than I do.
I’m not sure this would be the issue, but Gmail, by default, categorizes mail and puts them in various folders. Check those folders, especially the “Important” folder. The irritating thing to me has been that Mail on iOS now does that by default (I understand it will be the default in the next update of MacOS) for iCloud mail and Gmail. I find it VERY irritating and have spent huge amounts of time trying to find emails that I knew had been received only to find them in a folder.
If only it was that straightforward.
Gmail has no concept of folders. Each user account has one great big bag of messages. You can assign tags to messages. Every categorization, including “Inbox” and “Trash” are tags. And a message can have as many tags as you want.
When you connect via IMAP, the “folders” you see are all what Apple would call “smart folders”. Each one presents the set of messages that have a tag matching the folder’s name. So a message may exist in many folders. If the message has no tags, then you will only find it in the “all mail” folder, which presents everything that does not have the “Trash” tag.
The Gmail web interface is the same. No folders, but a list of tags. Clicking on a tag from the left-side margin filters the display to show only those messages that have that tag.
This is very different from all other mail services, which have actual folders. On those services, a single message can only exist in one folder at a time, and the folders you see in IMAP mirror the folders on the server.
Thanks for the clarifications!
The emails I have sent that disappeared were normal everyday communications with family and businesses, no change in content or tone for years, so I’m not sure how the Apple outgoing spam filters would have IDd my emails as spam. Would have been nice of them to inform me that happened, especially as I have no history of spam.
The Malware possibility, not sure how it could happen, I don’t think I had any attachments or if so only routine jpg/png/pdf in small sizes. Sending through a VPN, is that even possible that after I sent the emails something could be attached without my knowledge?
This is looking more and more like my sending of emails was shut down without notification for some reason so I might have to try Support. Want to get it narrowed down to dates in question but as noted, reaching recipients has been going slowly.
There has been a lot of different kinds of blocking activity going on with major email providers (Gmail especially, but also Yahoo, etc.) over the last 14 or so months – in an effort to protect their users from spam & scams. Those of us maintaining our own mailing lists, through our own domains have found ourselves changing our DNS properties repeatedly so that sent email isn’t dropped – silently, at least. But Google, especially keeps changing their rules and what they blacklist.
The main thing email users can and should do is to make sure – whatever app or program they’re using to send email – that their outgoing server is one of those authorized by the DNS of the fully-qualified domain name (FQDN) of the sender. I.e., in the SPF, DKIM, and DMARC DNS records for that domain or subdomain.
This applies to you, whatever FQDN you’re using on outgoing mail envelopes and From addresses. If it’s your own domain, and you’re not doing this, you need to read, for instance:
https://www.godaddy.com/resources/skills/configuring-dns-for-email-a-quick-beginners-guide
If you’re not using your own domain, you still need to make sure that the initial outgoing mail server is that of the mail service you’re using. E.g., if you’re using Gmail – and your return address is somebody@gmail.com – make sure you’re outgoing mail server is one of Google’s Gmail servers. If you use Apple’s Mail to send messages like that, it will generally use Apple’s mail servers for your outgoing mail. I’m not quite sure how to fix that, but a quick fix if you’re using @gmail.com addresses is to use either a Gmail app or Gmail’s web service (via any browser) to send your outgoing email. [FYI, if the browser you’re using is not Chrome, Google will often ask you to change it to Chrome.]
Turning Settings > [your name] > iCloud+ > Private Relay to On can sometimes also help.
@bob32 thanks for the detailed info!
I don’t need iCloud + so Private Relay isn’t an option afaik.
With a clearer head I did some more troubleshooting today and spent couple of hours chatting with 7 Apple Support reps.
I tested sending from all Apple Mail aliases on a MBAir I am slowly transitioning to and Mail sent and rec’d everything. So it seems only on the MBPro is sending an issue.
It seems the SMTP Server on the MBP in Mail App doesn’t want to stay on. I select the long-in-use iCloud Server in Account > Server Settings and seconds later it switches to None. I have no idea when this happened and reps could or wouldn’t say. I don’t recall turning it off or even know how to.
Connection Doctor shows account connects, a green dot.
When I go into Edit Server List, iCloud does not appear in the list of other email accounts so does not appear editable. When I click + to add a server, there are fields for details which none of the Support reps would provide.
I rec’d links to a couple of support articles in the Chats and nothing was applicable or helpful, but one remains to be tested later, removing and re-adding the account, which seems extreme and potentially troublesome; I count on the app for personal and business communications.
All of the reps used the familiar Apple chit-chat tone and were rushed, asked for a moment to review the case and asked questions that were already addressed with previous reps in the last hours. They must be under a lot of time pressure, but with each I explained that a successful solution was better than a fast solution.
One suggestion Support had was a phone call and screen sharing with the Escalation team. I explained I didn’t want anyone poking around in my Mac and I like Chats as I can save and review chats; I can’t save and review a phone call or send a screen shot.
I suppose I’ll take the risk on deleting and re-adding the account, after a full set of backups, and report the results.
Update:
I cleaned up the Inbox, moved a bunch of it to On My Mac, backed up, deleted the iCloud account in Mail and shut down the MBP.
Some hours later I booted the MBP and added the account back and Synchronized the account. It appeared to have repopulated the iCloud Inbox with the same mail I’d left there.
The SMTP Server in Settings remained on iCloud and did not change itself to None, so I had great hope success had occurred.
But…
I composed a test message from the icloud account to 3 non-Apple accounts and clicked Send. Got the swoosh sound but even half hour later the test message did not arrive at any of the other Inboxes.
So I’m pretty much at a dead end. That email account on the MBP seems unusable for Apple/iCloud email, as it indicates sending but it doesn’t really do it, or it seeps out of a pipe along the way ;-)
Accounts with other email providers on the MBP continue to work fine.
Check these:
You are logged into iCloud, even though you “don’t use it”, right?
Are the sent messages showing up in “Sent Mailbox”, as should be set in:
Settings → Apps → Mail → Mail Accounts → iCloud → Mailbox Behaviors
(Update: Oops, that’s the iOS or iPadOS path in the line above. There’s a similar setting in macOS, I think under Accounts.)