From: maryandliam on
if i send an email to someone with a gmail address they never receive it. it
goes to my sent items and it says sent in the properties but they never
receive it? any help greatly appreciated
From: Brian Tillman [MVP-Outlook] on
"maryandliam" <maryandliam(a)discussions.microsoft.com> wrote in message
news:E11EF0A0-CDE5-46F4-A0FD-979144D1590D(a)microsoft.com...

> if i send an email to someone with a gmail address they never receive it.
> it
> goes to my sent items and it says sent in the properties but they never
> receive it? any help greatly appreciated

If Outlook moves the message to Sent Items, then it WAS sent and whatever
accepted it from Outlook is not delivering it. One of two things will cause
this. The first is an antivirus scanner. Uninstall your AV program and
reinstall it without any mail scanning feature. If that doesn't help, then
speak with your mail service provider because it would be their server
refusing to pass it onward.
--
Brian Tillman [MVP-Outlook]

From: VanguardLH on
maryandliam wrote:

> if i send an email to someone with a gmail address they never receive it. it
> goes to my sent items and it says sent in the properties but they never
> receive it? any help greatly appreciated

When sending an e-mail, it first goes to the Outbox folder. If Outlook
receives an +OK status when transferring the message to the mail server, the
item is moved to the Sent Items folder and Outlook is done. Outlook can't
do anything more after sending the item to the mail server and being told by
that mail server that it got the message okay.

The question is what mail server got the message. If Outlook connected to
the real mail server, Outlook was told the mail server got the message okay
so Outlook is done. Some anti-virus programs operate as pseudo-mail
servers. Rather than intercept the e-mail traffic byte-by-byte to
interrogate it for malware, it pretends to be the mail server and accepts
all of the message. After interrogation, it pretends to be the client and
then transfers the message to the mail server. I believe McAfee operates
this way. So while Outlook as the client got an +OK status, that was from
the pseudo-mail server for the AV program, not from the real mail server.
You have to go look in the logs for your AV program to see if it, when
pretending to be the client, got an +OK status from the mail server. Better
would be to disable the superfluous e-mail scanner in your AV program.

As a test, you could Bcc a copy of a test message to yourself. Create an
e-mail account at Gmail. Create another account elsewhere, like Hotmail.
Neither of these test accounts should be on the same domain as from where
you send your test message. You want to ensure that no local shortcut
routing is used to deposit the test message in the target account. Send the
test message To your Gmail account and Bcc your other account. If you get
the test message that was Bcc'ed to your other account, you know that
Outlook successfully transferred your message to your real mail server and
that your real mail server sent out your test message. If you don't get
that same test message at your Gmail account then start looking at the
Junk/Spam/Trash folders using the webmail interface to your Gmail account.
If you don't find a copy of your test message in your Gmail account using
the webmail client, it is possible that Gmail is blocking e-mails sent from
the mail server for your e-mail provider; however, usually that means the
sender gets back a NDR (non-delivery report) noting that your e-mail (since
you were the sender) was rejected, so you might have rules or filtering that
is blocking you from seeing those NDR e-mails.