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Outlook delayed send not working at 12:05AM although all settings look right.

We have a user who is trying to send a "delayed send" message from Outlook 2003 SP2 not in cached mode. She sends the message as a particular distribution list to another distribution list. She sets the message up to send at 12:05AM and it doesn't send. When the message is discovered to still be sitting in the outbox in the morning, it is opened and resent from the outbox and it goes. Our dilema is to figure out why the message doesn't send when it was scheduled. We are on Exchange 2003 on Windows 2003 servers. We have re-installed the client, re-done the profile, tried it from different pc's, combed through all the "send as" permissions on the distribution lists, and still find nothing that would cause us to believe it wouldn't work. Is there something we are overlooking??
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svmEMDS
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svmEMDS
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peakpeakCommented:
Split the problem into smaller parts:
1. Can she send delayed fom her to one recipient (herself)?
2. Can send send from her to a distribution list?
3. Can she send from a distribution list to herself?
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svmEMDSAuthor Commented:
Yes, we have done all of the above. She can send delayed to other users and groups without any problem. She can send as the distribution list that ultimately fails at 12:05AM. I don't think we've tried having her send messages to herself since messages to others works.
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peakpeakCommented:
Please explain the use of sending from one distribution list to another. The list you're sending from contains multiple recipients so it must address more than this "another distribution list". Otherwise it's sufficient to just send to the "other" list as an address
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peakpeakCommented:
Things to check:
Regional settings (date, time) on server, DC and client
Database maintenance not running on the server 12:05
Does delayed work at other hours?
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svmEMDSAuthor Commented:
I know it seems like a very odd set up, but it works. I'm not sure of the logic behind doing it this way, but it's the way they want to do it and there's not a whole lot we can do about that, I'm sure you understand. So, the individual that sends the message has "send as" permissions to the distribution list, which is universal in scope (we're only dealing with one domain). The distribution list that she's sending to can only be sent to by the distribution list she's sending from. So, it's restricted.  This setup does work as we have seen this message go out manually and using delayed send in the past. Also, we have other set ups like this that go out daily successfully.
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svmEMDSAuthor Commented:
I will double check the Regional settings (date, time) on the server, DC. I know the client setting are current and correct.
Database maintenance starts at 12:00AM.
Would the database maint cause a delayed message to break?
It would seem inconsistent if it did on this particular server but not on the others.
Delayed does work at other hours, but we are restricted in our use of the actual distribution list to test, so we can only test with other distribution lists. So, far all of those tests have worked. I'm not sure if we've tested with a different list but sent at the same time frame. I will check that out.
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peakpeakCommented:
Send As is a bit unstable. I understand you want the messages to origin from a certain address. We solve it by creating an account with this address, set the rights for certain users to open the mailbox and in the user account for each user add this account to be opened. Now, when creating a new message you can choose in the drop-down list which account to be used. This is free from the glitches that is often caused by the Send As permission.
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svmEMDSAuthor Commented:
OK, the regional settings are ok. We changed the regional setting on the DC involved to simply "Central Time" instead of "Central Time, Central America", but both were GMT -6, so I don't believe that to be an issue, correct??

I thoroughly agree with your solution to this and it's much more solid from a performance standpoint. However, our current policy is to keep the mailbox to user ratio one to one for security reasons. As much as we would like to make a change in this, it's not one of the options we have at the moment. Maybe in the future, but not at the moment. We will have to make this particular set up work like it has in the past.
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peakpeakCommented:
Please try setting the delayed send to like 12:15
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svmEMDSAuthor Commented:
Oh, also, she can send using the delayed send during the same 12:05AM time period successfully to other distribution lists.  Other groups in our organization can do the same with their distributions successfully as well.
Would the ability to expand or not expand the particular distribution list play a role in whether the message makes it out on time?
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svmEMDSAuthor Commented:
We will certainly try setting the time for 12:15 AM.
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peakpeakCommented:
Expanding the list is (in my humble view) just a graphical difference. The content is the same. But then again, please try both. 12:15 AM was just a suggestion, better yet set it as far from 12:05 as allowed, then back up a notch each day
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svmEMDSAuthor Commented:
This is now resolved. When a user sets up a message for delayed send, it goes into the outbox and sits. If the user opens the message while it's in the outbox and closes it without clicking on the send button, it will fail to be sent when the prescribed time rolls around. We made sure the user left the message completely alone after it went into the inbox and the message was delivered just fine. Very interesting indeed. Thanks!
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