Optonline does not receive my Mac Mail

Question

Level 1

4 points

Optonline does not receive my Mac Mail

I use Mac Mail for various email addresses (comcast, gmail, mac/me) and I usually have no problem sending mail.

I have had a problem not getting a person using Optimum (Optonline.com) to receive any of my emails. It just does not get to the person (he's in his 80s, so I can't just say "get a gmail account") I receive mail from him just fine, but if I reply or start a fresh email, it just goes into outerspace, with no indication that it gets bounced, returned, or anything.

I did have success by using Moble Me WEB interface rather than my SOFTWARE Mail interface. Which leads me to believe it is related to Optonline not liking something that Mail is doing to the email???

This is a client, so its kinda embarrassing to keep wondering if they got my email etc.

Thanks, Dennis

iMac 24" 2.33 ghz intel core 2 duo, Mac OS X (10.4.11), MacBookPro 15" 2.9ghz; iPhone 3Gs, iMac 2007.

Posted on Jul 1, 2011 8:44 AM

Reply

Answer 1

Best reply

BobTheFisherman

Level 9

79,237 points

Jul 1, 2011 8:55 AM in response to Dennis Bolt

I think you have his email address wrong. If as you say you don't get any error, notifications, etc. then the email address you are sending to exists, only it is not his. Or, he has a filter/rule that discards your email. Or, you have something in your email that is seen as malware or otherwise dangerous and his or his ISP's spam blocker is silently discarding your email as a result.

Reply

Answer 2

Jul 1, 2011 10:35 AM in response to Dennis Bolt

If you have not already, try opening the Sent message, clicking on Message/Send Again, followed by clicking on Format/Make Plain Text, and then click to Send. If the message has previously been Rich Text Format, it probably is triggering something that is then blocking the message.

Ernie

Reply

Answer 3

Dennis Bolt Author

Level 1

4 points

Jul 1, 2011 12:57 PM in response to Dennis Bolt

Thanks Bob and Ernie

I have his address correct, because the problem exists even if I REPLY to his mail. Nothign gets there.

BUT when I tried the Web-based version of .Mac/Mobile Me it went thru. The only difference was that the failed transmission came from the SOFTWARE based "Mail" program that is part of the Snow Leopard, which I used happily for 8 years. I wonder if there is some kind of formatting/preference that Mail interjects that Optonline thinks is evil? I have never knowingly, had this problem with any other recipient.

Reply

Answer 4

Jul 1, 2011 1:03 PM in response to Dennis Bolt

My advice to change to Plain Text is meant to specifically address that possible formatting issue -- have you tried that?

Ernie

Reply

Answer 5

Dennis Bolt Author

Level 1

4 points

Jul 1, 2011 1:40 PM in response to Ernie Stamper

Hi Ernie

My default setting for Mail is Plain Text. I tried it again and made sure I sellected all and changed it to Plain Text, and it did not change the look, so I assume that no RTF snuck in. We'll see if it makes it.

The main trouble is that my recipient is not a troubleshooter and is in his 80s so my exploration at the success/failure has to go at his pace and ability. Sometimes I'm not sure if he actually gets it or has just ignored my email;-)

Reply

Answer 6

Jul 1, 2011 2:01 PM in response to Dennis Bolt

Keep us posted.

Ernie

Reply

Answer 7

Jul 1, 2011 9:17 PM in response to Dennis Bolt

It sounds to me like the email you're sending directly from your Mac is getting blocked by a SPAM filter somewhere along the way. If your outbound SMTP server, or perhaps your personal IP, has been blacklisted (RBL), it is quite possible that Optonline is simply rejecting your email. This would also explain why you succeed when sending from webmail, which will be sent from a different server that isn't blacklisted. If you know your IP address and the IP address of your outbound SMTP server, you can check their blacklist status on SpamCop and SpamHaus.

Reply