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Outlook 2010 on Exchange 2003 and Delayed Delivery Emails

I have one user in my organization that has about 550 emails in her outbox for future delivery.  What they are for - medical appointment reminders to others within the agency for our clients.  She uses both Outlook on her "regular desktop" as well on the terminal server (Windows 2008).  Outlook 2010 on both, using Exchange 2003 on Windows Server 2003.  Sometimes, she will get a batch of emails "undeliverable" to staff that no longer have emails in the organization.  When we have staff turnover (frequently) she has to go into the outbox and remove the staff that is no longer at the location/organization and put in the new staff.  Sometimes, these emails will be from 1-2 months late in their undeliverable status or 1-2 weeks.  The undeliverable message is just that she can't send to that person as they don't have an email.  When she looks in her sent messages, it does not show that it was sent to that person, but the people it was supposed to go to.  She is not using cached mode on either instance of Outlook.  I don't know if it is an Exchange issue or an Outlook issue.  She is the only person within the agency that has that many delayed delivery messages.  Others may have one or two, most have none.  I think she used to have cached mode on, but I turned it off so in case the message was sent and outlook happened to be closed for some reason.
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StephanieFoster
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StephanieFoster
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2 Solutions
 
Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
Look it could be that someone had the long gone user as delegate or in some rule thats triggering this NDR's

- Rancy
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StephanieFosterAuthor Commented:
She has no rules set up and no delegates.
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
It isnt on the sender its more on the recipient :(

- Rancy
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PostmasterCommented:
Recipients are checked at the time of send. If delayed send is used, their is the chance of confirming a mailbox ID that no longer exists when the "sent" email time arrives and it is processed.

Would it not be better to send a message with a follow-up reminder built in?
Or even a Calendar appointment?

Using such long delayed sends does not seem like a good practice.
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
Yes you can surely send a message with a Followup reminders along :)
Calendar appointment would only make sense if sent individually as that needs to be accepted and update done to calendar

- Rancy
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StephanieFosterAuthor Commented:
The only problem with sending a calendar appt or flagged/followup message would be if the person no longer works for us, which happens (unfortunately) quite a bit.  Or they change locations and then the next person would not have that information.  We are in a fairly high turnover rate business (non-profit, social services).  I am open to anything that would make this easier.  Some of these reminders are for next year already, for annual appt reminders.  

As for rules/delegates - those that are coming back undeliverable, the accounts have been deleted completely.  I purged the mailbox(es) from the System Manager.  It's like when the undeliverables come in, it was "flushed" out of somewhere because it doesn't happen regularly.  

thanks
Stephanie
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
I do understand Stephanie but to auto track and resolve itsnt which i think can be made possible by anymeans :(

- Rancy
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StephanieFosterAuthor Commented:
After Postmaster and Rancy suggested a calendar appointment, i've been testing that option.  I might have her test a couple locations.  She would just have to use filters to find the staff who she sent the the "invite" to, and then remove the staff it is no longer applicable to, add the new staff and resend.  

I'll see if that works for her.  If not, any other thoughts about why it would be sending emails to staff that don't have an account any more?  

Thanks
Stephanie
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