Weird Outlook problem

sszzish

So this problem stumped the IT department at my job lol & I can't find any help online about it...

I set up an Outlook account for my work email (which was a pain in a half, I had to reset my password twice until it recognized my account, don't know why). Now, about 75% of my emails are sent exclusively to my original work account (accessed through the browser) and the remaining 25% are sent exclusively to Outlook. I can send outgoing messages through either without a problem, but it's a toss up as to whether someone responding to that email gets sent to Outlook or the other one.

And strangely enough, as far as I can tell every person that sends me an email only ever gets sent to one account (e.g. emails from my boss are always sent to the original account, emails from one of my coworkers are always sent to Outlook).

double-u tee eff is happening here?? I'd be satisfied if emails were sent to both places, or even if they were just exclusively sent to one (even if it's the cruddy browser version of my account).

bowen

Well, sounds to me someone isn't updating the email address in their contact list. Personally I'd remove the old e-mail.

If you're saying that there is only one e-mail address and half of the stuff shows up in the web side and the other half in outlook, well, that is a wtf moment.

AtomBomb

Are you sure you have both set to leave messages on the server?

altmann

could be an MX record issue. If one is coming in from outside your network it may be getting routed to one account whereas inside the network is going somewhere else.

sszzish

haha yep, one email address.

I tried looking into setting both to leave messages on the server, but Outlook doesn't give me the option to (these websites direct me to change account -> advanced settings but to no avail) and I wouldn't even know where to begin to look for the web version (which uses Squirrelmail).

Would deleting my Outlook account help? I'm afraid if I do so, then emails will just be lost forever instead of redirected back to the web version.

I don't know what a MX record issue is >.<

ashridah

if this is one single email account, do you know if it's being accessed via POP or IMAP? I'm guessing POP, since that explains the behavior you're seeing most easily.

POP is more like a mail delivery box. if you take things out, you can't take them out a second time, unless you look at them and put them back in (poor analogy, but relatively apt, nevetheless).

Basically, the best solution here is to use IMAP instead of POP. IMAP's designed to use a folder structure on the mail server. You'll need to make sure your mail server can handle the amount of mail you'll wind up storing on it over time, however. (you'll want several GB of space at least, for a moderately active account these days, that gives you lots of breathing room). Outlook can be setup to archive stuff locally, so older stuff automatically gets copied off, but new stuff should be accessible to both clients.

sszzish

My email has 50 mb of space, pretty lame!

I don't know whether it's POP or IMAP. I looked up how to find out on Outlook, but where it's supposed to say it, it only says "Microsoft Exchange". Squirrelmail's website says it requires an IMAP server to run on top of, but is able to retrieve emails from a POP server (so this means it can't send emails to Outlook via POP? I guess?)

http://squirrelmail.org/wiki/SquirrelMailFeatures

MrDelish

sounds more like an MX record problem to me than POP, especially if you're receiving specific addresses' messages at each location

I'd imagine your IT department would be better able to help you than we are, especially since we have no information on the domain you're using or your company's email structure; perhaps you should escalate it there somehow?

bowen

This is almost definitely a POP issue. MX record issues wouldn't be there for a single e-mail address. Most likely one is pulling emails off the server and the other one obviously can't see those e-mails because once retrieved they're deleted.

Think of it like a Post Office (It is the Post Office Protocol after all). If you go check your mailbox at 1:00 and then your dad goes to check it at 1:05, he won't see the mail you've already picked up.

MrDelish

If it were really a POP issue then he wouldn't be getting any messages at all on webmail unless he coincidentally has Outlook closed at the time/Outlook isn't checking for messages right then (or after, since they'd disappear then, too). Assuming he's correct in saying that specific addresses' messages are being delivered only to either webmail or Outlook the problem could only be from a DNS issue.

fake edit: though I have no experience with Exchange servers, this can't be a POP issue since he's using an Exchange server, right?

actual edit: Google says you can have POP3 enabled on an Exchange server. Still doesn't change that the consistency in which he gets messages from addresses to each place he checks his email can't solely be a POP issue, though

bowen

I assume he's closing outlook and then using the webmail. By default most people will set up POP account on the email server. If he's got both open at once, it just depends how fast one can download over the other.

Exchange servers can be interfaced through Exchange/outlook directly (X.500?), IMAP, or POP so it doesn't really make a difference to the server, but matters completely on what each client is doing to the data. The fact that he said it's a single email account makes me doubt an MX issue.

Exchange and IMAP function similar, but if that webmail is set up as POP or to remove the emails once they're downloaded, then, that would explain the missing emails.

Edit: As for the specific senders, I'm not sold on that being an issue. Sounds to me like maybe the person(s) might send email at a specific time and that's when he's doing all his testing. Personally I'd stop using webmail completely and just see if all the emails start showing up. That'll tell you right away what kind of problem it is.

sszzish

I keep the Outlook and web email open at the same time almost all day at work (so I don't miss if an email is sent to either one). But there have definitely been times when I only have one open (especially Outlook, since I'll often close the web version during lunch or even by accident for an hour or so, while Outlook stays on all day without me touching it), as well as times when neither are open...it doesn't seem to change what gets sent where and by whom. I guess I really haven't tested it that hardcore tho.

BlazeFire

Do this:

close Outlook and the webmail interface.
send your work e-mail a message from another e-mail address (something like gmail).
Open outlook and get new messages. Did you get the message from yourself?
close Outlook.
send your work e-mail a message from another e-mail address (something like gmail).
open the webmail interface. Did you get the message from yourself?

oh, then post whether you got the two messages.

bowen

Yeah the more and more you describe your process the more and more it sounds like a POP issue.

Do what Blaze says.

sszzish

Okay I emailed my work email 1) with neither opened, 2) with both opened, 3) with Outlook opened, and 4) with the web version opened. I did this from two separate email addresses (gmail & yahoo). All eight emails were sent to the web mail.

Also, I have noticed that I have ONLY ever received an Outlook email from someone using a work email address. While I often get emailed from work email addresses to the web version, I also get any other address sent there too. Which fell in line with my gmail/yahoo emails only getting sent to the web mail. Is it possible that I only get emailed to Outlook if the other person is emailing with Outlook with their work email?? Does that make sense?

MrDelish

I can't imagine this being a POP/sync issue. I have customers that get this kind of problem when their MX routing is set to local but their server/MX entry aren't with us; ie, the mail gets delivered to where their site is instead of their mail server.

Ruckus

sszzish wrote: »

Okay I emailed my work email 1) with neither opened, 2) with both opened, 3) with Outlook opened, and 4) with the web version opened. I did this from two separate email addresses (gmail & yahoo). All eight emails were sent to the web mail.

Also, I have noticed that I have ONLY ever received an Outlook email from someone using a work email address. While I often get emailed from work email addresses to the web version, I also get any other address sent there too. Which fell in line with my gmail/yahoo emails only getting sent to the web mail. Is it possible that I only get emailed to Outlook if the other person is emailing with Outlook with their work email?? Does that make sense?

Tell us what version of Outlook you're using and we'll tell you how to find the "Leave Messages on Server" feature. I'm with Bowen on this sounding like a POP issue.

MrDelish

How can this be a POP issue when he's not even getting the messages on Outlook? Webmail is strictly IMAP, meaning that if he's getting the messages on webmail but not Outlook the problem is almost certainly not from a POP connection.

sszzish

Ruckus wrote: »

sszzish wrote: »

Okay I emailed my work email 1) with neither opened, 2) with both opened, 3) with Outlook opened, and 4) with the web version opened. I did this from two separate email addresses (gmail & yahoo). All eight emails were sent to the web mail.

Also, I have noticed that I have ONLY ever received an Outlook email from someone using a work email address. While I often get emailed from work email addresses to the web version, I also get any other address sent there too. Which fell in line with my gmail/yahoo emails only getting sent to the web mail. Is it possible that I only get emailed to Outlook if the other person is emailing with Outlook with their work email?? Does that make sense?

Tell us what version of Outlook you're using and we'll tell you how to find the "Leave Messages on Server" feature. I'm with Bowen on this sounding like a POP issue.

I use Outlook 2010, but if you were going to say to do something like: http://www.slipstick.com/mail1/leaveonserver.htm , I already tried. There's no option to leave messages on the server via the advanced settings window that site guides you to. It's just not there, I don't know why. Unless there is another way you are talking about.

NailbunnyPD

Without knowing what kind of server arrangement you have handling and delivering mail, I think all troubleshooting suggestions here are just shots in the dark.

Its possible the efforts here are misdirected. Could this SquirrelMail thing be snatching the emails from the server before Outlook can see them?

There's just a lot of information missing here.

Ruckus

NailbunnyPD wrote: »

Without knowing what kind of server arrangement you have handling and delivering mail, I think all troubleshooting suggestions here are just shots in the dark.

Its possible the efforts here are misdirected. Could this SquirrelMail thing be snatching the emails from the server before Outlook can see them?

There's just a lot of information missing here.

I'm fairly certain SquirrelMail is still just a PHP webmail app that just accesses the user mailbox on a mail server via IMAP. It can't really download anything off the server, it just shows you what's in there. I do wonder if the SquirrelMail retrieval marks them as read/downloaded and thus Outlook ignores them when it communicates with the server.

bowen

I don't think we're getting all the information. It's quite possible his email address on the server is not set to receive email addresses and I'm not terribly sure how it's all set up.

But now that you're saying that the webmail is getting it, it does seem more like an MX issue. Which is a job of your IT department.

sszzish

Maybe if I go back to my IT department with some sort of knowledge or direction they will make a more substantial effort to figure it out...thanks everyone for trying to help me troubleshoot this, I appreciate it

bowen

Here's what it sounds like to me:

From outside the office, the email hits the MX record, goes to the server that it points to. This happens to be the squirrelmail server. From inside the office, the internal LDAP/Exchange system detects your external e-mail as one that it supports delivery too, so inter-office emails work fine. You sending out will also work.

Why the MX record is differentiating between you and everyone else in your office is confusing. It may just be someone fucked up a DNS record somewhere, or, there is a DNS entry that hasn't updated yet (can take up to a week in some parts of the world).

NailbunnyPD

bowen wrote: »

Here's what it sounds like to me:

From outside the office, the email hits the MX record, goes to the server that it points to. This happens to be the squirrelmail server. From inside the office, the internal LDAP/Exchange system detects your external e-mail as one that it supports delivery too, so inter-office emails work fine. You sending out will also work.

Why the MX record is differentiating between you and everyone else in your office is confusing. It may just be someone fucked up a DNS record somewhere, or, there is a DNS entry that hasn't updated yet (can take up to a week in some parts of the world).

Neither SquirrelMail or Outlook are server products that will receive mail via an MX record. There is a mail server (or servers) configured in between here. SquirrelMail and Outlook grab mail from the server.

Also, I'm not aware of any configuration that would allow one email address to have a one off MX record. MX records are established for a domain.

If I had to guess (and again, this is a shot in the dark without more information,) there seems to be a race between SquirrelMail and Outlook to grab the mail from the servers. Or, There is some odd forwarding going on, where the receiving server is forwarding mail to another server. Outlook might be pointing to that receiving server and, sometimes, grabs the mail before it has a chance to be forwarded.

Again, not enough information to properly troubleshoot.

bowen

I did say the servers. He already ruled it out the race condition.

I think the squirrelmail system is sitting on top of another mail server that the MX record is pointing too. Which would explain why internal emails work in the exchange/outlook setup and only external mails are showing up in squirrel.