Outlook 2007 behaves as if it's on an Exchange server!

[Ichinisan]

I should probably post this in the Networking forum...because those guys probably have experience supporting MS Office 2007.

Cliffs:
Config'd Outlook 2007 to send using Gmail's SMTP server; different server for POP incoming.

Works perfectly from my system, but Outlook 2007 mangles the display name when the customer uses the same config. OL2k7 is botched somehow!


I work for a small local cable ISP. The company that currently hosts the email for us has the worst SMTP server I've ever known. "FAIL" sums up everything about the SMTP server.

If there's even one invalid recipient address, the message will not leave the Outbox. Often, the pop-up error message doesn't even show the failed address. Sometimes the error is as vague as "550 and has been rejected" [sic]. Sometimes the message appears to go out, but the "Undeliverable" message comes back with a dozen names and "451 Temporary Local Problem - Try again later." We've had non-stop problems for more than a year. The email folks don't seem to understand how unusable it really is. All this, and our system also gets blacklisted by every other mail system whenever there's a hint of a compromised user. They treat our system as if it's some small office instead of an ISP.

Anyway, this has created HUGE problems for our commercial customers, especially local businesses with mailing lists.

The planned transition to Google's commercial email hosting services is the only hope I've had. All year long, I've been told "it will happen really REALLY soon." I just have no clue how much longer it's going to take.

Today, I finally tried to work around the issue by creating a Gmail account for a customer, allowing them to authenticate with Gmail's outgoing server. In their email client software, we configured the Gmail SMTP settings. It's still set to our server for incoming mail. It worked great. I have it set so only the original email address is presented to the recipients.

After the success for the first customer, I called another chronic commercial customer. For some reason, when she sets up Outlook 2007 with Gmail's SMTP, it mangles the display name:
"TJ's Discount Meat & Seafood TJ's Discount Meat & Seafood [removed@gmail.com]; on behalf of; TJ's Discount Meat & Seafood [removed@numail.org]"

I tested the same configuration using Outlook Express on my workstation, then tested using Outlook 2007 on a co-worker's workstation. I confirmed that Gmail's server is not re-writing the subject...it's her Outlook 2007 email client.

I Googled "outlook+2007+on+behalf+of" and found that this should only apply to accounts on an Exchange server. The customer uses POP...and it's just a small corner store, they definitely would have no use for an Exchange server. Our employee emails use Exchange, but this setup worked fine when I tried it on a coworker's system with Outlook 2007.

 

[SpatiallyAware]

It sounds like you're using hosted email? And you're an ISP with a ton of accounts using said email service?


......You need to find someone at your email hosting that knows wtf they're doing. Good luck, dealing with these hosted exchange setups are a major PITA.



Why don't you guys have your own exch server?

 

[Phynaz]

Nevermind, I mis-spoke.

 

[minendo]

Did she set up a secondary account in Outlook or did she change the appropriate settings for the outgoing server? I've seen this issue when a secondary account was set up and then used to send email instead of properly configuring outgoing server settings.

 

[Nothinman]

If there's even one invalid recipient address, the message will not leave the Outbox. Often, the pop-up error message doesn't even show the failed address. Sometimes the error is as vague as "550 and has been rejected" [sic]. Sometimes the message appears to go out, but the "Undeliverable" message comes back with a dozen names and "451 Temporary Local Problem - Try again later." We've had non-stop problems for more than a year. The email folks don't seem to understand how unusable it really is. All this, and our system also gets blacklisted by every other mail system whenever there's a hint of a compromised user. They treat our system as if it's some small office instead of an ISP.

Without knowing exactly what errors and bounce-backs you're getting it's hard to say what's going on. But other than the 451 error, the rest may be by design and may not even come from that server. If a remote server gives a 451 error when your host's server tries to deliver to it you're going to get that bounce back. If there's content filtering or you try to relay through that server from a place it's not configured to allow relaying for, or without authentication, then you should get a 550 error. Not all errors mean the server sucks or is misconfigured.

Today, I finally tried to work around the issue by creating a Gmail account for a customer, allowing them to authenticate with Gmail's outgoing server. In their email client software, we configured the Gmail SMTP settings. It's still set to our server for incoming mail. It worked great. I have it set so only the original email address is presented to the recipients.

After the success for the first customer, I called another chronic commercial customer. For some reason, when she sets up Outlook 2007 with Gmail's SMTP, it mangles the display name:
"TJ's Discount Meat & Seafood TJ's Discount Meat & Seafood [removed@gmail.com]; on behalf of; TJ's Discount Meat & Seafood [removed@numail.org]"

I tested the same configuration using Outlook Express on my workstation, then tested using Outlook 2007 on a co-worker's workstation. I confirmed that Gmail's server is not re-writing the subject...it's her Outlook 2007 email client.

I Googled "outlook+2007+on+behalf+of" and found that this should only apply to accounts on an Exchange server. The customer uses POP...and it's just a small corner store, they definitely would have no use for an Exchange server. Our employee emails use Exchange, but this setup worked fine when I tried it on a coworker's system with Outlook 2007.

I just tested that here with mutt and it did the same thing when I changed the From header to my alternate email address. I'm guessing your successful customer used their gmail address in the From header.

 

[MrChad]

http://gmailblog.blogspot.com/2009/07/send-mail-from-another-address-without.html

 

[Ichinisan]

It sounds like you're using hosted email? And you're an ISP with a ton of accounts using said email service?

We used to host our own email system. We were switching to a new system for small cable operations to manage...everything. That company typically hosts email for their client ISPs and it made sense for us to switch because we were outgrowing our system anyway.

It turned out to be a bad idea, but there's no easy way to go back. It has been this way for a little over a year now. The current email host is planning to transition their own system to Google's commercial email hosting...but that has been delayed-and-delayed forever.

......You need to find someone at your email hosting that knows wtf they're doing. Good luck, dealing with these hosted exchange setups are a major PITA.



Why don't you guys have your own exch server?

We do. For our employees. There's no Exchange server for customer email. I was complaining that a customer's Outlook 2007 install behaves AS IF it were on an Exchange server. It should not behave that way. It's just using regular POP/SMTP.

Did she set up a secondary account in Outlook or did she change the appropriate settings for the outgoing server? I've seen this issue when a secondary account was set up and then used to send email instead of properly configuring outgoing server settings.

Only one account configured in Outlook 2007. Our server for incoming (POP), Google's server for outgoing (SMTP).

 

[Ichinisan]

Without knowing exactly what errors and bounce-backs you're getting it's hard to say what's going on. But other than the 451 error, the rest may be by design and may not even come from that server.

I've been analyzing these errors for more than a year. I know when our SMTP is at fault. It's actually a relief when the SMTP error is a response from the REMOTE server. It often doesn't get that far!

I just tested that here with mutt and it did the same thing when I changed the From header to my alternate email address. I'm guessing your successful customer used their gmail address in the From header.

I don't know what you mean. The configuration in Outlook for both customers was as follows:

Email address:
ours

Incoming server:
ours

Outgoing server:
gmail's

Outgoing authentication:
LOG ON USING: [gmail account]

The Gmail accounts both have sender info set in the Gmail account settings. It sends messages in a way that presents only our email address to the recipient (the gmail address is never presented and never receives any mail).

So, basically, the Gmail account exists only to allow my customer to authenticate with Google's SMTP server.

 

[Ichinisan]

http://gmailblog.blogspot.com/2009/07/send-mail-from-another-address-without.html

Hmm...that wouldn't be a solution because it would be sent through our barely-usable SMTP server that I'm trying to avoid using.

I don't understand...that seems to suggest that Gmail changed the display name to show "on behalf of"...but then why does it only do that for ONE of the customers I set up this way? Very strange.

 

[Nothinman]

Hmm...that wouldn't be a solution because it would be sent through our barely-usable SMTP server that I'm trying to avoid using.

I don't understand...that seems to suggest that Gmail changed the display name to show "on behalf of"...but then why does it only do that for ONE of the customers I set up this way? Very strange.

The link says that Outlook displays it like that, I'm guessing your other client got lucky and their recipients don't use Outlook.