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jasmo34
join:2008-03-20
~ London ~

jasmo34

Member

Outgoing Emails to Hotmail missing, or delayed

Are messages from TSI to Hotmail being held or delayed by Hotmail for some reason? Anyone else encountering this? Does Hotmail use this deliberate delay technique?

Is there a particular email screening service that Hotmail might use, that I could check? Nothing shows up at MXToolbox, where TSI's email servers sometimes show up on a blacklist check. (btw, I am sending via smtp.pppoe.ca.)

I had one message I sent yesterday afternoon, which only showed up this afternoon at Hotmail. Two more tests I sent today (6 or 7 hours ago) are missing. One of those test messages DID arrive at the other recipients (yahoo mail, mail.com), with no delay. Other emails are making their way into my Hotmail account, with no delays.

It's kind of ironic, that I BCC myself some of my 'more important' outgoing emails to my hotmail account, to help me troubleshoot my 'normal' email problems with TSI. And now those BCC emails are disappearing at Hotmail, along with some other test emails.

(Again, I know... don't use ISP email! I am slowly abandoning TSI's email!)

DrZEUS
join:2004-01-13
Mississauga, ON

DrZEUS

Member

Yep happening to me too. I had tech I was speaking to on the phone yesterday who was sending me a couple of emails for something else and they never came. I asked him to send to another address and they appeared instantly.

Fast forward to today and those emails appeared time stamped with the today's date and the time they came in today.

Definitely something going on.

TwiztedZero
Nine Zero Burp Nine Six
Premium Member
join:2011-03-31
Toronto, ON

TwiztedZero

Premium Member

This also happens on Yahoo mail and Gmail. I've noticed when I send or recieve messages to friends on blackberries, the several hour delay, particularly on recieving end of things. This has been ongoing for some time now.

jasmo34
join:2008-03-20
~ London ~

2 edits

jasmo34

Member

OK, looking at and comparing some email headers...

That first message of mine went from TSI to yahoo in 14 minutes; that same message from TSI to hotmail took 22 hours.

Another missing message has now shown up at Hotmail; TSI to yahoo was seconds; TSI to hotmail was 9 hours.

I've had my share of email problems over the years; this seems different. And this didn't happen a couple days ago. I send this exact type of email about 3 times a week.

I've had emails I send to rogers.com (yahoo email?) experience hours delays; I've had emails I send FROM yahoo rejected/delayed, because of spam problems at yahoo. I don't think I've ever experienced any delays using gmail, in either direction.

Anyway, is Hotmail rejecting my emails from TSI for some reason, but ironport (TSI) keeps trying to send them until they do finally get through, and that is the timestamp I see at Hotmail?

Or is the delay actually in the outgoing IRONPORT servers (at TSI's end)? But why would they delay the same email only to the Hotmail recipient, and not the Yahoo recipient?

As I mentioned before, emails sent from other sources (yahoo, mail.com) are getting through to my Hotmail account with no delays. Only the TSI to Hotmail emails are delayed/missing.

edit1: my last missing test email from TSI to Hotmail has now shown up, in about 4 hours. The delays may be getting shorter, from TSI to HMail, but this same email was delivered to yahoo email and mail.com in seconds!
jasmo34

1 edit

jasmo34

Member

TSI Direct Forum Support is not aware of any email delay problems that may have been happening. I'm the only one who reported this problem. And of course, no delays are apparent today in my tests, or their own email test today.

Support suggested it might be a problem with the email clients I used (Outlook Express and Windows Live Mail). I didn't know using Outlook Express could cause the one copy of an email BCC'd to Hotmail to be delayed 22 hours, while the other BCC was delivered to Yahoo in seconds, and the TO recipient got his in seconds. And other emails (not from TSI) were getting through to Hotmail just fine during the delay period. Maybe I clicked on the wrong SEND button or something...

Oh well... just another little TSI email 'peculiarity'.

I'll be there soon, GMail!