Outlook 2010 and Mail Sticking in the Outbox

This is a non-network question for Outlook 2010. I am not using an Exchange server. I am set up at home using Outlook 2010 on a home cable connection. Every time I send an email it hangs in the Outbox. There are no errors.
If I go to the Outbox and send it from there it sends without a problem. I have tested the cable router and line with no problems. Do you think it could be a problems with Outlook itself? Please advise.
Michael T. Glenn

Hi,
I suggest you disable the firewall and anti-virus program to try again, they are more likely to cause this kind of issue.
Moreover, there are several steps that we can try to troubleshoot this issue.
We can start Outlook in Safe Mode to determine if it's 3rd-party add-ins related:
Press Win + R and type “outlook.exe /safe” in the blank box, then press Enter.
If there’s no problem in Safe Mode, disable the suspicious add-ins to verify which add-ins caused this issue.
Please also run Scanpst.exe to repair your Outlook Data File to check the result:
http://support.microsoft.com/kb/272227/en-us
We can also create a new profile to re-setup your email account:
http://support.microsoft.com/kb/829918/en-us
Regards,
Melon Chen
TechNet Community Support

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Outlook 2010 - sending mail with attachment - "The system cannot find the file specified"

Hi forum Fellows,
I have the following failure scenario:
1. A user receives an e-mail with an attachment.
2. The user opens the attachment --> Forwards the mail and writes something in the body of the e-mail
3. For whatever reason the user leaves the e-mail and works on something else --> the user comes back to the e-mail an hour or more later.
4. The user then wants to send the e-mail but gets the following error message: "The system cannot find the file specified"
5. The effect is that the user cannot send the e-mail.....
------------------------------ TROUBLESHOOTING -----------------------
- I can see that when the user opens an attachment this attachment is saved in the OutlookTemp folder. Actually, there is a difference between opening the attachment before or after clicking forward on the e-mail.
---- Before: Two files is written to the OutlookTemp folder. For example if the attachment name is FileX.pdf - there will be a FileX.pdf but also a FileX (2).pdf in the folder (if OutlookTemp is empty/do not contain a file with the name FileX.pdf already)
---- After: Only one file is written to OutlookTemp. That is FileX.pdf
- Running Process Monitor when trying to forward the e-mail I can see that Outlook is calling a file that is not in the OutlookTemp folder anymore.
**** To me this is the heart of the issue. For some reason, when a user has an e-mail with an attachment open for an extended period of time (not sure on exactly how long is necessary), files in the OutlookTemp folder is deleted - files that Outlook is depending
on to be there.
- Going with a totally clean OutlookTemp folder does not help.
------------------ NOW WHAT ---------------
- The question now is: Is this by design? Can it be fixed by some Outlook 2010 patch? Or perhaps a group policy/registry setting as a workaround.
------------------------------ TECH. INFO -----------------------
Outlook 2010 v14.0.7132.5000
Outlook bit depth: x86
Running on a 2008R2 SP1 TS environment.
No antivirus on the TS
Looking forward to hear from you.
Regards The Red Baron
Red Baron

Hello Red Baron,
Although not a complete answer, the way to treat attachments in emails require some discipline:
1. Never open an attachment directly from the email (and NEVER edit it from there). Always save it in a known location as the desktop or (better) in a designated document folder. Then you can proceed as usual, like editing the contents, printing, forwarding
the new version etc.
2. Directly forwarding the attachment is ok, along with additional text in the body of the email.
3. Having any (unsaved) document open for several hours should
never occur. What if there is a power outage?
Bottom line is thus Discipline. This is regardless of Operating System (which might handle temporary files differently).
These are the rules I teach my customers and they never leave any document unsaved for hours ...
Best regards George

Using new computer, existing mailbox user Outlook 2010 Auto-configuration points to the Mailbox Server rather than CAS Array ?

People,
I'm having a problem with the current AD user account & mailbox user where they cannot get the Outlook 2010 automatically configured to point into the CAS array ?
This is happening when the existing user get new computer replaced or login to the Terminal Server where their account never set before, it always points to the Mailbox Server instead of the Client Access Server array virtual name.
The work around that I provided is typing the Client Access Array address and then specify Outlook.domain.com to match the Windows NLB name (and Get-ClientAccessArray result).
Single AD Domain forest
AD Site DataCenter contains:
Domain Controllers: PRODDC01-VM, PRODDC02-VM, PRODDC03-VM
Exchange Server 2010 SP3 - CAS&HT: PRODMAIL01-VM and PRODMAIL01-VM (Configured with WNLB as outlook.domain.com)
Exchange Server 2010 SP3 - Mailbox: PRODMAILBOX01-VM and PRODMAILBOX01-VM (no DAG is set)
Terminal Server (RDSH 2008 R2): PRODTS01-VM ... PRODTS60-VM (when user logged in to new TS, it got the same error).
AD Site HQ contains - This site has no issue:
Domain Controllers: HQDC01 and HQDC02
Workstations using Outlook 2010 and 2013
AD Site SiteOffice1 contains - This site has problem:
Domain Controllers: none but the majority of the workstations LOGONSERVER is pointing to PRODDC03-VM
Workstations using Outlook 2010 and 2013
All of the Exchange environment here is using Exchange Server 2010 SP3 for all server roles.
Any help would be greatly appreciated.
Thanks
/* Server Support Specialist */

Hi,
Yes, the RPCClientAccessServer should point to the CAS array. What's more, I would like to clarify the following things:
1. Run the Get-ClientAccessServer | fl AutoDiscoverServiceInternalUri cmdlet to make sure that it displays the correct Uri.
2. Run the Get-WebServicesVirtualDirectory | fl Identity,*auth*,*URL to ensure that URL for EWS points to the CAS array.
Hope this can be helpful to you.
Best regards,
Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact [email protected].
Amy Wang
TechNet Community Support
Here's the result:
[PS] C:\>Get-ClientAccessServer | fl AutoDiscoverServiceInternalUri
AutoDiscoverServiceInternalUri : https://PRODMAIL02-VM.domain.com/Autodiscover/Autodiscover.xml
AutoDiscoverServiceInternalUri : https://PRODMAIL01-VM.domain.com/Autodiscover/Autodiscover.xml
[PS] C:\>Get-WebServicesVirtualDirectory | fl Identity,*auth*,*URL
Identity : PRODMAIL01-VM\EWS (Default Web Site)
CertificateAuthentication :
InternalAuthenticationMethods : {Ntlm, WindowsIntegrated, WSSecurity}
ExternalAuthenticationMethods : {Ntlm, WindowsIntegrated, WSSecurity}
LiveIdSpNegoAuthentication : False
WSSecurityAuthentication : True
LiveIdBasicAuthentication : False
BasicAuthentication : False
DigestAuthentication : False
WindowsAuthentication : True
InternalNLBBypassUrl : https://PRODMAIL01-VM.domain.com/ews/exchange.asmx
InternalUrl : https://PRODMAIL01-VM.domain.com/EWS/Exchange.asmx
ExternalUrl : https://email.domain.com/ews/exchange.asmx
Identity : PRODMAIL02-VM\EWS (Default Web Site)
CertificateAuthentication :
InternalAuthenticationMethods : {Ntlm, WindowsIntegrated, WSSecurity}
ExternalAuthenticationMethods : {Ntlm, WindowsIntegrated, WSSecurity}
LiveIdSpNegoAuthentication : False
WSSecurityAuthentication : True
LiveIdBasicAuthentication : False
BasicAuthentication : False
DigestAuthentication : False
WindowsAuthentication : True
InternalNLBBypassUrl : https://PRODMAIL02-VM.domain.com/ews/exchange.asmx
InternalUrl : https://PRODMAIL02-VM.domain.com/EWS/Exchange.asmx
ExternalUrl : https://email.domain.com/ews/exchange.asmx
The IP address of email.domain.com and outlook.domain.com are the same IP address, this IP address is servec by WNLB.
/* Server Support Specialist */

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Email links in Firefox 5.0 will not auto open in Outlook 2010 AND Windows Live Mail 2011

Outlook msg: General failure. An error occured in sending command to the application.
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Many thanks jscher2000, problem solved.
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The setting Leave mail on the server and Delete after n days and Pressing Send/Receive all folders causes outlook 2010 to duplicate all mails of the last n days over and over again.
If I leave outlook 2010 open this problem does not occur, mail will be retreived without a problem. If I leave Outlook 2010 open for a long time and then press Send/Receive all folders it does work ok. If I restart Outlook 2010 and then press Send/Receive
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Dear Pieter,
I suggest creating a new Outlook profile, and create the problematic account in the new profile, to see if the problem occurs.
Here are the detailed steps on how to create a new profile to test this issue
==============
1.    Exit
Outlook.
2.    Go to
Start > Control Panel, click or double-click
Mail.
Mail appears in different Control Panel locations depending upon the version of the Microsoft Windows operating system, Control Panel view selected,
and whether a 32- or 64-bit operating system or version of Outlook is installed.
The easiest way to locate
Mail is to open Control Panel in Windows, and then in the
Search box at the top of window, type Mail. In
Control Panel for Windows XP, type Mail in the
Address box.
Note    The Mail icon appears after Outlook starts for the first time.
The title bar of the Mail Setup dialog box contains the name of the current profile. To select a different existing profile, click Show Profiles, select
the profile name, and then click Properties.
3.    Click
Show Profiles. Choose Prompt for a profile to be used.
4.    Click
Add.
5.    Type a name for the profile, and then click
OK. Please also follow the onscreen instructions to create the email account in this profile.
6.    Start
Outlook, and choose this new profile.
If this problem does not occur in the new Outlook profile, the old Outlook is corrupted. We can delete that and use a new Outlook profile.
Please take your time to try the suggestions and let me know the results at your earliest convenience. If anything is unclear or if there is anything
I can do for you, please feel free to let me know.
Best Regards,
Sally Tang

OWA receives mail long before Outlook (Exchange 2013 with Outlook 2010 and 2013)

I recently upgraded my Exchange environment to Exchange 2013 SP1. The Outlook users are now experiencing a delay when receiving email. When they do arrive they appear in batches, often 20-45 minutes after they were sent, from a mailbox on the same server.
Additionally, the mail appears instantly when you monitor the inbox using OWA. The users are experiencing this on both Outlook 2010 and 2013 clients configured in both cached and non-cached modes. This appears to be a problem with Outlook connecting to Exchange.
Any suggestion about how to correct this would be greatly appreciated. Thanks!

Hi,
From your description, when users use OWA, they can receive emails normally. But if they use Outlook 2010 or Outlook 2013, there is a delay in receiving emails.
I recommend you use the Outlook safe mode to determine whether the problem is caused by add-ins. Also, please make sure users have installed the Outlook latest Service Pack.
If the issue persist, please create a new profile and check the result.
Hope it helps.
Best regards,
Amy Wang
TechNet Community Support

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This may be helpful.
http://itconflict.com/2012/01/08/troubleshooting-icloud-sync-with-outlook/

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Easy solution for restoring lost calendar informaiton, thank goodness. On your iPhone, go to settings, then to iCloud. If your Calendar selection is turned off, turn it on. Your info should restore. If your Calendar selection is turned on, then turn it off. Choose to save calendars when asked. After it shuts the Calendar off, turn it back on. Your info should be restored.
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Salam,
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Kindly help me in this problem.
Regards,
M. Faisal

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pretty please....

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Michael

Outlook 2010 e-mail signature missing from reply

Hi!
I have create a signature, and it works fine when creating new emails. But when replying/forwarding, there is no signature attached. And this despite I have attached the signature under options->mail->signatures->Replies/forwards.
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Hello,
My users are experiencing the following issue:
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2. User closes Outlook 2010 for the day.
3. When user reopens Outlook 2010 the next morning, the message is still sitting in the Outbox and was never sent.
The problem is this was not the case with Windows XP/Outlook 2003/Exchange 2007 in online mode. Where the user would be able to send the delayed email then shutdown his/her computer and the message would be submitted and sent from exchange.
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Daviesw

I posted this on Microsoft home page as well. there is an issue with the plugins below. the stuff in gray is what led me to my solution for me below.
Disable AVG's addin - it's known to cause problems.
I have been using AVG for the past 5 years. I had the issue before I upgraded to AVG 2011. I've never had a problem until I moved to Office 2011. I don't recall if I stated using delayed delivery before I upgraded to Outlook 2010, however.
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I was having this problem as well. I did NOT have this plugin. but i got thinking about 3rd party plugins. I have the "Google calendar calender Sync" tool that syncs my outlook calendar and my Google calendar together 2 ways. As soon as i disabled this it went
through no problem. its possible that other 3rd party plugins are not allowing it to function as desired as well. i suggest disabeling all the 3rd party add-ins and and running a test. mine is now working like a champ

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I would suggest that some virtual directories configured to use Basic Authentication. EWS, OAB or Autodiscover for instance.
Also check Outlook Anywhere configuration. If it was changed from NTLM to Basic it could cause such credential's prompts.
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http://blogs.technet.com/b/get-exchangehelp/archive/2013/01/31/the-curious-case-of-maxconcurrentapi.aspx
http://blogs.technet.com/b/askds/archive/2011/09/15/is-this-horse-dead-yet-ntlm-bottlenecks-and-the-rpc-runtime.aspx
HTH

Outlook 2010 and Mail Sticking in the Outbox

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