Intermittent sending of email problem, restart of Outlook clears issue.

Not open for further replies.


I have a client with multiple PC's having this issue intermittently. I have had this problem in the past (years), and as I worked to find a solution, it happened to me again. This is not a new issue, nor is it an issue with the basic "setup" of the email accounts.

Intermittently, can be with a new email, or a reply, withor without an attachement, the mail will go to the outbox and this error will appear:

Task '(name of smtp server) - Sending' reported error (0x8004210B) : 'The operation timed out waiting for a response from the sending (SMTP) server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).'

whatever email is in the outbox is now stuck, and new incoming email will continue to come in. the only solution to the problem is to exit Outlook, Ignore the question Outlook presents telling you you have email in the outbox and would you like to send it before you exit (if you try, it fails) and simply start outlook again. this immediately sends all email in the outbox.

In my, and my clients case, we are both using CA ITM anti-virus and spyware, WITHOUT the email scanner. We are not using any added software firewall. This is Windows XP pro, and the Outlook 2003 is SP3 (I remember this issue going back years with no SP and SP2). the account setup is for a POP3 server, and there is basic SMTP auth and no SSL. Pretty basic stuff.

I have found search responses suggesting corrupted account, bad account config, and problems with server. I have read to use the logging feature to find the problem, and when I do all it suggests is that Outlook does not even try to send the email. I have looked into my email server logs (we are NOT using exchange, its a POP3 server) and there is NO entry of any attempt to connect to my server and SMTP the email. I have even changed the SMTP server name in the account settings to the IP address testing if its perhaps a DNS issue. it appears to me to be a total lack of Outlook even trying to make a connection to the email server, even as it reports the error suggesting it had.

there are a few searches that specifically suggest the SP2 and SP3 upgrades had actually fixed this issue, but it appears its back. This problem has become a larger issue as the client does not realize the email had not gone out and it becomes a time sensitve issue. I have been trying to find a solution for weeks, and it appears to be an Intermittment Outlook problem.

Does anyone know of a solution?

Kathleen Orland [MVP]

What happens if you open Outlook in safe mode, does the behavour continue?

Start > Run > outlook.exe /safe

(note the space between outlook.exe and /safe)



I have not tried safe mode, as this is a working environment and while its hitting 6 or so of the systems, its quite intermittent, some users have reported having to restart Outlook 2 or 3 times a day, another that had the issue multiple times a day just a week ago, is now seeing it perhaps once every other day.

this client is vry stong in the need of their email, and asking them to try to operate in safe mode (in Outlook) may be a hardship. I did have a user create the error log for me, and I found once the problem starts, Outlook just never seems to try to send the email, even though if you try to exit it asks if you want to send the email first. the fact an attempt was not being made was also noticed at the email server.



good thought, I have been running a continuous ping with the maximum MTU size for the last 20 minutes from their netwrok to mine (this is where the email server is) and so far aside from a very few drops, the MTU proves to be 1500, and I am having no issues.

this would still not explain why simply exiting and restarting outlook would clear the outbox and send all the email wihout fail, everytime. If there really was a blackhole router, I would assume this would not be the case.

I had experianced this issue a while back myself, and others mentioned the same thing. Since we could all simply restart Outlook I never really worried about it. This client however is having issues with it due to the timely nature of some of their email. I have always considered this an Outllook problem, and am suprised there is not much on it.

Somasundaram Pandiaraj

Rename the send/receive file (.srs) from the location mentioned below and verify the issue.

drive:\Documents and Settings\<user>\Application Data\Microsoft\Outlook
Not open for further replies.
Thread starter Similar threads Forum Replies Date
E Multiple, intermittent Outlook 2010 errors Using Outlook 12
G Outlook Intermittent Issue with Drafts not Displaying Entire Content Using Outlook 4
K Intermittent ability to send to single domain. "Connection refused" Exchange Server Administration 1
E intermittent "Your imap server closed the connection" messages Using Outlook 6
C New mail icon on taskbar intermittent Using Outlook 1
T Problems WinRM on Microsoft Exchange Server 2010 - Showing errors then success messages intermittent Exchange Server Administration 4
D Intermittent Connection Between Outlook '03 and Exchange '03 Using Outlook 5
G A problem with intermittent Outlook connection Using Outlook 1
D Sending email from Office 365 alias in Outlook Using Outlook 4
E Change sending account depending on Subjectline Outlook VBA and Custom Forms 0
L unblocking attachments before sending Office 365 Advanced Protection Using Outlook 0
B Outlook 2003 email sending & receiving suddenly stopped working Using Outlook 3
R Warn before sending message Outlook VBA and Custom Forms 4
HarvMan Hotmail - Sending email is undeliverable Using Outlook 4
A Sending contact vcards sends older version instead of updated version Using Outlook 4
M McAllister Outlook stops Sending/Receiving/Synching after disconnecting remote desktop session Using Outlook 2
D Adding Enterprise Exchange Email Account to Outlook Prevents Sending via Account Using accounts in Outlook 10
B When sending an email, I am showing 2 of my address's Using Outlook 1
M Auto expand Distribution List Before Sending Email Outlook VBA and Custom Forms 1
A Check for words in subject header before sending email Outlook VBA and Custom Forms 4
O Run macro automatically at sending an email Using Outlook 11
W Sending To Wrong Account Using Outlook 15
H Select Specific Account When Sending Email, Based on Current Folder Outlook VBA and Custom Forms 1
M Help sending email but removing signature via VBA Outlook VBA and Custom Forms 5
M MsgBox when not sending from specified account Outlook VBA and Custom Forms 2
A Script to fetch data from mails in restricted collection and sending them to excel Using Outlook 1
R Sending emails via Outlook XP, from Windows 10 File Explorer Using Outlook 1
L Creating drafts when I thought I was sending Using Outlook 1
C address book "when sending email" bug? Using Outlook 0
H Custom autoforwarding, sending mail through outlook office 365 Using Outlook 1
R Sending email copy (*.msg file) of sent email if subject line contains specific string. Outlook VBA and Custom Forms 1
C replace subject line generated by converting a word document to PDF and sending it to an email Using Outlook 8
A Sending Emails Through Outlook From Multiple Email Addresses Using Outlook 1
P Outlook 365 sending intermittently Using Outlook 0
C How to avoid sending mail to the wrong contact person New Articles 1
V iCloud Calendar invitations not sending Using Outlook 3
O Rules and Alerts for New Messages BEFORE sending Using Outlook 2
latitudeit Outlook for Android - Sending from an alias address Using Outlook 2
X Delay sending an email until the next working day (public holidays) Outlook VBA and Custom Forms 0
D Macro sending outlook template from Excel list Outlook VBA and Custom Forms 6
A How to get rid of "sending on behalf of" when sending from Outlook 2016 client Using Outlook 12
O Outlook 2013 Problems sending large mails Using Outlook 4
Diane Poremsky Automatically create a task when sending a message New Articles 0
P Categorise emails on sending - macro not working in Preview mode Using Outlook 1
Diane Poremsky Outlook is sending winmail.dat attachments New Articles 0
Diane Poremsky Select from a List of Subjects before Sending a Message New Articles 0
P Outlook 2010 sending safe senders email to junk box Using Outlook 8
Diane Poremsky To delay sending a message in Outlook New Articles 0
F Avoid sending duplicate using Outlook script Outlook VBA and Custom Forms 2
D Close Oulook after sending emails via vba without outbox getting stuck. Outlook VBA and Custom Forms 1
Similar threads