Foo - any Outlook email gurus in da house?

I am running MS Outlook 11.8217.8221 sp3.

When my wife sends me an email and I try to reply to it, I get the following error message

Your message did not reach some or all of the intended recipients.

Subject: Tonight
Sent: 7/31/2009 10:27 AM

The following recipient(s) could not be reached:

'Mxxxx xxxxxxxxx' on 7/31/2009 10:27 AM
550 5.7.1 n6VFQx4W008184 This message does not comply with required standards.

The xxxx are where I x'd out my wife's name.

Any ideas of what I can do. This only seems to occur when replying to her. Most other people, I can reply to, or at least I am not getting an error message.

Geez, I hate Outlook.

But, are there some oddball characters in the email address or message?

If it's your wife's work email it could be on that end. That's a similar message to what I used to get when I tried to send email to where my wife used to work. They really had where emails could come from pretty limited.

Not that I can tell. This just started occuring. Up until this week, I could reply to her. Now I can't. It is pretty much just her email address from her office/blackberry that I can see. I can reply to emails she sends from her personal address. And she is not having problems getting replies from other people for emails sent from her work/blackberry.

Try sending an email to your wife from an online email like gmail or yahoo or hotmail or something.

If that works ok, try sending an email from your outlook to that web email.

Should narrow down which end is the problem.

I can send her new mails. I can receive mail from her. I just cannot reply to mail from her.

our IT guy (the support one, who fixes things, not the 'architect', who sets it all up) suggests we have all our work email forwarded to a gmail account and handle it from there rather than outlook/exchange. Apparently gmail has mail forwarding both ways, so outgoing mail will still look like it's coming from exchange, or something like that.

our IT guy (the support one, who fixes things, not the 'architect', who sets it all up) suggests we have all our work email forwarded to a gmail account and handle it from there rather than outlook/exchange. Apparently gmail has mail forwarding both ways, so outgoing mail will still look like it's coming from exchange, or something like that.

Wow......what a horribly cumbersome solution just because he can't fix it. :(

Wow......what a horribly cumbersome solution just because he can't fix it. :(

YouTube - Seven Mary Three - Cumbersome

Wow, I even derail my own threads. Does that make me a bad person?

BTW, that was shot about a mile from my house. I heard them playing as I sat in my front yard.

It sounds like she may have a "reply-to" address that's different than her regular e-mail address.


First things first. Send an e-mail directly to her known address through Outlook. Don't use a webmail, we need to make sure that outgoing e-mail works through your regular client to her address.

That should work. Now, we need to find out what her "reply-to" address is.

Find an incoming message (one you would reply to) in the list of e-mails. Click the e-mail to highlight it, then right-click the e-mail. From the pop-up menu, click on "Message Options". A dialog box will come up; we don't care about most of what's in it. At the bottom of the dialog, there will be a text box containing the original message headers. You need to copy and paste these headers into this thread.

Sanitize the headers, obviously, but please don't remove any more information than you need to. If you're not sure what should and shouldn't be sanitized, feel free to PM it to me, and I'll clean it up and post it.


If she does have a different reply-to address, it should be specified in the headers. If she doesn't, there should still be some useful information in the headers.


Finally: the e-mail you're getting with the error message, "The following recipient(s) could not be reached". Is this e-mail coming from your mail server, or from hers? If you're not sure, copy and paste the headers from that e-mail as well.

TJ, check your PM. Oh, and thanks for the help, I really appreciate it.

Just sent a message to my wife, she replied to it, but I cannot reply to her reply. Not sure if that means anything. There is no header info on the error message I get in outlook when I try to reply, just the text I posted in my first post here.

outlook sucks...pigeons are much more dependable.

Outlook does not eat my sunflower seeds and **** on my desk, other than that, I agree.

It might be an issue with your server authenticating hers. She might not be in the same mode (SMTP) as you. See the following link and search for the error message.

http://social.technet.microsoft.com/Forums/en-US/exchangesvrtransport/thread/1a84a06a-f1c8-40b4-ace8-1e264f218aa1

Also, her server might reject any references to phases like, "wanting your hot sweaty body" and "can't wait to see you soon you sexy thing" :rolleyes:

:innocent:This is my wife I am talking about, not Pgoat and MV.......:innocent::rolleyes:

Some Exchange servers are set up to use dedicated send/receive connectors. However, I looked this up, and a misconfigured connector wouldn't do this message. However, a squirrley third party add-on might cause this 502 error.

Can you use another mail client than Outlook? I know my home Exchange server supports IMAP, webmail (OWA), and POP3, so I can use one of those protocols to check for issues, bypassing Exchange/Outlook for mail testing.

That particular error is a "relaying denied" error. You are trying to send mail out through a remote server and it's denying the request. There are TWO email severs that you need to configure in Outlook:

POP3 is the incoming email server at your ISP
SMTP is the outgoing email server at your ISP

These are configured from the settings given to you by your ISP and might even be the same server. If the outgoing SMTP server requires authentication, you must have the ISP-account's user-name and password entered into Outlook to use for sending out mail. Note that this might be a different user & password from your email name & password.

Also your recipient's email servers and domain have NOTHING to do with how you set up your Outlook configuration. As others said, send a new message to your wife and type in her correct email address manually and see if it gets through correctly.

Outlook has a stupid feature that hides the actual email address from you. I could send you a message that has different FROM: and REPLY-TO: addresses and the reply-to address is typically faked with spam messages. When you hit the reply button, it populates the TO: box with whatever's in the REPLY-TO: field of the original email. It could very well be "Jsharr's Wife <spammer@getfreemoney.com>" and it would still look OK to you and Outlook... until you try to send.

Here's a useful article: http://support.microsoft.com/kb/287532
There's also a problem with Outlook when it's configured with internet-mail only without an Exchange connector. I suspect it's intentional since MS wants to sell Exchange Server software rather than giving away Outlook for free.

Also what anti-virus software are you using? Do you have email-scanning turned on? If so, turn it off and test email-sending to your wife again. Some anti-virus software re-configure your Outlook settings to send mail in & out through their servers and bypass your ISP. Which the ISP may not like.

I can send email to her work address just fine. I can send email to her home address just fine. It does not matter if I type in the address or select it from the address book. I can receive mail from both. I just cannot reply to her work adress. I can reply to her home address generally. It is only one address that appears to be affected.

I can send email to her work address just fine. I can send email to her home address just fine. It does not matter if I type in the address or select it from the address book. I can receive mail from both. I just cannot reply to her work adress. I can reply to her home address generally. It is only one address that appears to be affected.

might be an issue on her end then.
Have her send an email to a hotmail or gmail account and then see if you can reply.

jsharr -- sorry I haven't gotten back to you sooner, I've been away from my computer.

According to RFC 2821, SMTP reply 550 indicates a general failure, specifically "Requested action not taken". Error code 5.7.1 (RFC 1893) indicates a permanent failure; the delivery is Not Authorized, and will not be retried. In other words, something went wrong with delivery, and we're not going to try it again.

Exchange typically uses 5.7.1 to indicate a relay error, but neither 550 nor 5.7.1 is relay-specific.


I don't see anything remarkable in your message headers, except for the fact that it doesn't look like you're using Exchange. It looks like you receive your e-mail from a qmail POP3 server. I imagine you send to an SMTP server.


Googling around, this seems to be a pretty random error. A number of people have experienced it against a number of e-mail servers. I have not yet noticed a pattern or a solution.

Workarounds seem to include making minor changes to the e-mail, much of it to the body of the message. Adding or removing characters, that sort of thing. I doubt you'll have substantial luck with random changes, however.

It would probably help if we knew what SMTP server you were configured to send through. Go to your Tools menu, and click on Account Options -- this will get you into the e-mail account options. Where to go from there depends on your version of Outlook. If you need help, let me know what you see on the screen and I'll walk you through where you need to go. Again, what we're looking for is your SMTP server (either domain name or IP address). It will also be helpful to know if you are authenticating to your SMTP server.

It looks like you use secureserver.net as your e-mail host. If that is the case, please check your configuration against their instructions here (http://products.secureserver.net/email/email_outlook.htm).

My ISP is CenturyTel. We also have a GoDaddy acct so that we can get usfoamcorp.com as our email address. However, I am sending and receiving from that account via Outlook and the server is the Centurytel server. I can send and receive to everyone. I can reply to everyone but my wife's work address. I do not think it is a set up issue, since it is so selective.

I also can send from my centurytel address to my godaddy address successfully and I can respond from my godaddy address to my centurytel address, all from Outlook.

I think I forgot to mention, this seems to be an error with the mail server (rather than with Outlook).


Try this (strange, but recommended by several people): reply to an e-mail. Remove the "Re:" from the subject line. Try to send the e-mail.

Still having the problem. Have followed all kinds of guides, including those sent by TJ and nothing seems to help. I can reply to all emails except those from my wife and now to one of our sales reps.

Anyone have suggestions for e mails programs to replace Outlook? Need to be able to configure it to use my centurytel and godaddy email addresses here at work.

I have been known to reply with "your message could not be delivered", too... when its someone I don't want to deal with :innocent: just sayin'.

Valid point.

I finally removed all teh boiler plate and links to insurance products that accompany any mail she sends me from her office, and lo and behold, my mail goes through. Not sure why it works, but it does.

Sounds like some Exchange filter that checks for bounces or backscatter. At least it can be worked around.

That's somewhat back to my original idea. Funny though that replies to HER will go through after removing the stuff that HER email tacked on. A system that blocks it's own stuff? If so there must be an IT guy with a bad sense of humor.

If so there must be an IT guy with a bad sense of humor.

Doesn't that describe about 99% of us IT guys?

I finally removed all the boiler plate and links to insurance products that accompany any mail she sends me from her office, and lo and behold, my mail goes through. Not sure why it works, but it does.


Good. This is a good thing, you're able to manipulate it.

Can you try to figure out a sort of "minimum" change that has to occur for this error to pop up? That is,


your wife sends you an e-mail.
change nothing, you get an error.
delete two lines, you get an error.
delete four lines, you don't get an error.
so, delete three lines. do you get an error?


If you can get it to the point where you can say, "when this happens, I need to make this change" then you're in really good shape.

Once you've made a few tests (say, 4 or 5) so you can show a few that work and a few that don't, I'd say you should contact your local IT. From what I've read, this seems to be a problem with your mail server, not with your wife's. Whether that's true or not I can't say with the limited info I have access to. If you have no local IT, I would contact your ISPs help desk. It's reasonable to expect your ISP to offer some support on a problem like this.


You're likely to get a better response from them if you approach them with "this is my problem, here's what I've done to try to fix it, here's what I've found" than if you just say "I can't reply to my wife's e-mail".


Good luck!

I've seen this before.
Your computer has developed feelings for you and wants the wife out of the picture.

Secure 24/7 Online Access: www.GuardianAnytime.com (http://www.GuardianAnytime.com)


that is the line that caused all the blockages. Anyone have any ideas why having that link to a secure log on page would cause my outlook or ISP to not send a reply?

So when that line is in the e-mail you can't reply, but if you remove that line the reply goes through?


Forward that information on to your ISPs tech support. The answer is really going to depend on what e-mail server they're using. They'll also be able to tell you if the problem is their mail server or your wife's.

If you're their only customer having this problem, there's a chance it won't get fixed -- patching an e-mail server for one customer isn't going to be high on an admin's list of things to do. But they may take it seriously, and if nothing else they should want to know about it in case it happens in the future.

I sent them an email detailing my problem. but my expectations are very very low, based upon past interfaces with what Centurytel calls customer service.

That's somewhat back to my original idea. Funny though that replies to HER will go through after removing the stuff that HER email tacked on. A system that blocks it's own stuff? If so there must be an IT guy with a bad sense of humor.It's not his wife's email-servers that's block stuff. It's adding on signature lines which then gets blocked by his ISP's mail-server when he replies. They're just blocking what they think are spammers and relay attemps.