Outbox messages disappear and are not stored anywhere

Question

0
When users are offline and send emails, they are kept in outbox, when they connect to the network the messages in outbox are sent. No problem here. the problem happens when, for some reason the outlook freezes when connected back to the network. the user
must close the outlook and when it opens again the messages arent in Outbox or in sent items. They arent delivered also, we checked that.
Can you help me fix this problem?
Thank You
Miguel Silva

Answer 1

I'm having the same issue.  It's happening almost daily with me. As noted by other users above, I am able to continue receiving emails during this time. 
The instance that caught my eye with this, happened the other day.  I ran into a colleague and asked about a message I had forwarded a few minutes before.  She hadn't gotten it.  I thought perhaps I'd sent it to her home mail, so I went back
to my sent box to check.  It wasn't there.  I checked my desktop thinking perhaps I hadn't hit Send, but no.  That's when I noticed I had 8 messages in my Outbox.  I was docked.  I could actively get to the Internet and our internal
servers.  On the bottom status bar in Exchange it said "All Folders Up to date.  Connected to Exchange Server."  And yet, Outbox held 8 messages. 
I went and got our user support person at that time, so another set of eyes could confirm this.  I can't remember what we did next, but we got the "Outlook not responding" message.  We closed Outlook, got the message that there was a problem,
do you want to wait for it or close and restart where you left off.  I clicked on close and restart.  When it restarted Outlook opened up a couple of windows of emails I'd read awhile ago. They were mails that I'd opened and left open while I worked
on the issue referenced in the mail.  So they'd probably been open for anywhere from 5-15 minutes.  But I'd long since closed those couple open emails from my desktop.  I saw that my Outbox cleared of those 8 messages, so I went to my Sent
box, and they weren't there.  It had probably been 45 minutes since my last sent message.  However I was receiving emails the whole time.  I was opening and reading the new mails, deleting them, and even replying to them, without noticing that
the replies weren't leaving my Outbox.
Our user support person recommended that I delete and recreate my .OST, which we did.  That kept me working for one day before the problem returned.
Couple things I've noticed.  I get the "Outlook not responding" and have to restart Outlook mostly when I'm moving email to my .pst on a network drive. 
I rarely undock this laptop, so I'm not going into standby or using WiFi.  However I have noticed in Event Viewer I will get Informational Event ID 26, "Connection to MS Exchange has been lost.  Outlook will restore connection when possible." 
followed by another one "Connection has been restored."  The drop of connection has never been longer than 2 milliseconds.   I might be able to equate the drops to that loss of connection, but it seems I have to do something else at the same
time, as the drops are much more frequent than the not responding/data loss problem.  (probably get 8-10 drops / day, but only see this Outlook not responding/loss of email 1-3 times a day.)
Upon suggestion of my Exchange Admin I've turned on return receipt so I can hopefully catch it in the process and at least be able to hopefully remember what emails I'm going to have to recreate. 
This is a big deal for us!!  We suspect I'm not the only one having this problem, as 3 of my lost emails were calendar requests, and since moving to Outlook 2010 we've been getting a marked increase in people complaining of meeting notices they
aren't receiving.  So I'm trying to actively monitor it while I get my work done today.  If there's anything you want me to trouble shoot, please let me know.
Regards,
Barb