[REQUEST] Couple of Funky Gmail Issues

G8racingfool

Well-Known Member
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Location
Oakland NE (No not CA)
Okay so I've got a client who uses Gmail to send/receive email (it's actually my town's city office who I'm trying to get onto an MSP plan to take care of all this crap through O365/Exchange but I digress) to other official orgs. Problem is, she's having trouble with some email recipients.

The first (and my primary concern) one, the email appears to send but after about 24 hours bounces back with SMTP error 442 (Connection dropped during transmission). Since it's Gmail I'm assuming this is due to spam filtering on the recipients end. My client uses the webmail interface to send email so it's not like it's piping through the office network or is any sort of local connection issue. The recipient does use some sort of hosted domain (unsure of what atm, attempting to find out) so spam filtering would be my best guess. What do ya'll think?

The second one is really weird. Emails from my client, who again is using Gmail through the webmail interface in Chrome are occasionally getting black-holed when being sent to the recipient who is also using a Gmail account and vice-versa. I honestly have never seen an issue with Gmail2Gmail before. Both addresses are plain Gmail accounts and there are 0 bounce-backs, errors, or other evidence of any kind of failure. Both users (client and recipient) swear up and down that they've checked everywhere in their inbox/spam/archive/etc and there is nothing to be found. IIRC, Gmail doesn't drop mail ever. It either bounces back or delivers the mail so this one's got me scratching my head.


My solution would be to register a domain and move them over to O365 with an MSP plan and be done with it. City council isn't on-board with that yet though so I'm stuck trying to figure this out for now.
 
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