As there are a lot of smart people on here, I’m hoping someone can suggest what I’m missing with this email delivery issue affecting my wife. She is not receiving some emails and I cannot understand why.
Here are the key points of the setup:
The email address in question is a Hover mailbox.
The Hover mailbox is set up to forward all email to a Google address, and not to keep a local copy.
The Hover mailbox was (inadvertently) configured to do its own spam filtering, but the spam was being left in the inbox at Hover where I can see recent examples. This has now been corrected to allow all senders (allowing Google to make the spam decisions).
Google is configured to allow sending from the Hover address.
Now to the issue:
Some types of emails from a local auction site (like eBay, but not eBay) are not arriving at Google. (The important ones, of course.)
Other types of emails from the local auction site do arrive at Google.
The missing emails are not found anywhere in Google (neither Spam nor All Mail nor Trash).
The missing emails are not found anywhere in Hover.
With that in mind, a few other points about the setup:
Google has no filter rules that delete emails.
There are no filters defined at Hover.
Earlier this year I set up Cloudflare on the domain in question, however, this should not affect email and the emails have not been delivering since October last year. Also, manual test emails from multiple people (and many other automated type emails) are arriving just fine.
We went through the auction site’s troubleshooting steps and everything is as it should be. Their last step suggested changing the email address on her account. We changed it to one of mine, then attempted to change it back. Now we need the confirmation email for that last change which… you guessed it… hasn’t been delivered.
First, disconnect Gmail from the system. Do the missing-type emails show up in the Hover account? If not your problem is almost certainly there.
Second, give the auction site her Gmail address instead – ie, leave Hover out of it. Do the missing-type emails show up? If not, you have a problem in Gmail.
Thanks. Both of those have complications, but I think I can manage them with care:
Disconnecting Gmail will leave ALL emails at Hover and then I will need to get them moved later, but a quick test can minimise this. The “change my email address” confirmation should give me a quick way to test.
The Google address is used on another account at the auction site and they don’t allow them to be the same, but I wonder about the old user+something@google.com approach.
Yes, I have but thanks for suggesting. She uses Gmail’s web interface only.
I just did @tf2’s item 2 using a +tm on the address and that is successfully delivering, so it’s something at Hover apparently. Which is a worry considering I have just moved myself and my two kids to Hover, and mine forwards to Gmail, too.
Speaking of Hover, their usually great support seems to be faltering at the moment. I have two support tickets open with them that are going nowhere.
For all but one issue, my many years with Hover email have been everything I could hope for. Hover support, in my experience, has always been friendly and responsive but not always immediately effective.
I tried some different spam settings once with my Hover email account to “see what difference it would make” as the settings were not explained adequately in Hover’s documentation. What a mistake! My advice is to leave the spam settings alone on Hover email. I now manage spam in my Apple Mail account after downloading all my email from Hover.
I had to work my way up to higher levels of Hover support staff and eventually got my account “reset”. But it was another month for everything to be straightened out again. (It felt like a thirty day timer of some sort had to run out before things were allowed to return to normal.)
Have you stopped the email forward to Gmail to verify whether it’s landing at Hover before forwarding?
As a mail server admin, honestly, if I were Hover that would be a required first step for me to even get involved in troubleshooting.
Gmail outright throws away some email without any trace, and forwards actively cause problems with Gmail’s trust relationship with the forwarding server. Which makes the “thrown away without a trace” behavior worse.
I can’t count the number of times my ability to troubleshoot missing email has ended with “Google is telling my server they received it just fine.”
Can I ask why you’re forwarding to Gmail instead of just using the hover account directly? It seems to me you’re adding a layer of complication in which things can go wrong (and possibly are), and I personally like avoiding those complications whenever possible.
At the moment we have the emails going direct to Google which gets the job done for now at least, and maybe even permanently.
That sounds frustrating and within the realms of possibility.
At some point I will go through another test with Hover set to leave a copy locally, but not for a while, as she’s happy and can do without me messing it up for a bit.
Multiple reasons.
The Google Workspace account came first — well over 10 years ago.
The Hover account is a much newer additional identity.
My wife knows the Gmail interface, and uses several of its features — Hover is very basic.
For my own, I have the same setup because I want the Gmail spam filtering and search prowess (and to use Mimestream on my Mac) but I want my own domain. I’m just not prepared to pay for both of my accounts and my two sons’ accounts on that domain. Well, I would be, but not to the tune of USD$288 a year.
And bonus points for Gmail being a royal pain to migrate away from. So much so that I’ve decided I am not going to migrate her even to a basic Gmail account because of the pain I went through with my own just last week doing that. Even just considering the “pre- and post-migration” pain — I’m not going to put her through that. Then there’s my pain in doing the migration, given Google don’t provide a simple way to do it.
I’ve got the same. I had to ask them how, but basically you add *@*.* to the allow list. I also set the spam box to Inbox so if anything was getting caught, it’d immediately be obvious when I log in.
On the Hover support front, they have got back to me on the older support request today and the outcome is every bit as good as I’d expected. They must just be snowed under — perhaps under-staffed due to illness and also maybe extra work due to Google.
This isn’t unique to Google. Any email server configured to use blacklists like spamhaus.com, and other filtering methods, will reject messages coming from spammers and malware sites without notifying the recipient.
“iCloud uses trend analysis, dynamic lists, and other technology to automatically detect and block junk mail before it reaches your inbox.”
Yes! My “allow list” is now full of the email addresses that went missing after I foolishly changed spam settings.
This is a very interesting idea, although at this point I am gun-shy about messing with my spam settings. My situation is stable so I think I’ll leave things alone.
I had a user that complained to her executive that she was missing “important” (i.e personal) emails. She was a senior employee and could be quite persistent when complaining. I was told to “fix her problem”.
So I stopped filtering everything except malware and she received around 300 spam messages in the next two hours.
I guess that’s my point - the emails aren’t going direct to Google. If you have a forward at Hover, the emails have to be received by Hover’s mail server, get packaged back up as outgoing messages, and then sent to Google.
Absolutely - not unique to Google.
The issue here is that the forward actively exacerbates the problem. You may already know this @WayneG, but I’m guessing most people don’t. Here’s the process:
Hover makes a determination whether to receive the email, based on the sending server’s IP, DKIM, DMARC, etc.
Once it receives the email, it consults its rules about delivery. In this case it sees that it’s supposed to forward to somebody@gmail.com
Hover packages up the email, and tries to deliver it to somebody@gmail.com
Gmail sees a request from Hover for it to accept an email to somebody@gmail.com
Gmail makes a determination whether to receive the email, based on Hover’s IP reputation, DKIM, DMARC, etc.
And it’s that last step that’s really the issue. Leaving aside DKIM/DMARC/SPF/etc., if Hover is configured to forward all mail indiscriminately, that means Hover is forwarding a bunch of spam. Which means Gmail sees Hover’s mail server as a source of spam. Which can cause Hover’s reputation to go down in Gmail’s eyes. Which means good mail from Hover is less likely to get through.
I run a mail server, and I’ve seen this happen. Customers never understand it, but it’s a huge problem.
In an ideal world, Hover would be doing spam filtering before forwarding. But since that’s been completely disabled:
OP’s world is far from ideal - and could actively be making the problem worse.
If the email isn’t time-sensitive (i.e. it’s okay for it to show up 30-45 minutes after it arrives at Hover), gating it to Gmail via Gmail’s POP3 integration is a far more reliable delivery method.
No. If you download email via POP3, that’s a different thing entirely from using SMTP to forward mail from one server to another.
In fact, Gmail supports checking email from other providers via POP3 as well - and that’s the alternative I recommend if somebody is currently using forwarding and it’s problematic. The problem with Gmail’s POP3 checking is that it fires at less-than-predictable intervals, sometimes 30 to 45 minutes in duration. So it’s not great for mission-critical email.
But if you have mission-critical email, you shouldn’t be using an email forwarding address either.
I will take a look, though not all email from the auction site is getting lost. Ironically, the more spammy ones are making it through.
I should clarify. We changed the setting at the auction site to send them direct to Google using a +variant email address (working around the fact that the ‘native’ Gmail address is used by another auction site account).
Ohhhhh! I see this now.
Unfortunately I see this now, too.
I have used this approach before for different situations — namely when Gmail has been the ‘real’ account and it POPs from an ‘old’ account that is earmarked for shutting down. I did not consider it at all for this situation but I can totally see how it changes the dynamic for the better. No, the emails are not time sensitive.
Further to all of the above, since I posted I also learned more about SPF records and realised I did not have one for her Hover domain. Until right now I thought that was only harming her outbound emails, but I now realise it was also likely harming the inbound ones in the forwarding scenario because they are also (perversely) outgoing. To Google.
Thanks @webwalrus this has been a real eye opener.
