That folder is the queue of messages, and SMTP service will handle delivery, retry, and NDR's, etc - Stop the SMTP Service: Open IIS Manager, right-click SMTP Virtual Server, then click Stop. Under this mode the SmtpClient will write to the SMTP pickup folder (something like c:\inetpub\smtp_root\pickup) instead of trying to deliver the mail itself.
Use SmtpClient and set the delivery method to pickup directory. if it's stuck in the queue, you can try smtpdiag to find out more information IIS 7 SMTP: Email in Queue Folder is Locked (Read Only) 02:25 AM There is certain retry logic in the smtp property setting, I forgot the actual setting, you can check the smtp property page.
SMTP Relay Failure - Messages stuck in Queue folder - The remote SMTP service rejected AUTH negotiation Hello, We have configured SMTP Service on our Windows 2008 R2 server to use to send emails and we created an account in Office 365 which is used to send emails and is also configured in the outbound security - > basic. I've moved them to the pickup folder but they end up going back to the queue Everytime I use IIS I change the IP addresses but the mail still gets stuck in the queue. The operating system I use is Win 2000 Pro.
The manual retry attempt overrides the next scheduled retry time.
Problem : Can you resend BadMail emails in IIS/SMTP Service? Is there any way I can move the emails out of the BadMail folder in IIS/SMTP server and into the Pickup folder so that they can be resent? I notice that for each bad email that gets dropped into this directory, three files are created (.BAD.iis 6 - IIS smtp messages stuck in inetpub/mailroot/queue Hi, Anything updates now? Which sutup you have followed? Did you mean that SMTP server didn't deliver the mail? If yes, please check the -delivery report -delivery report would be created in the C.We followed the setup provided by Microsoft but messages are stuck inside the queue folder. Reply We have SMTP relay server in IIS for office 365. After 2 straight days of troubleshooting I ended up stopping the SMTP server, deleting all messages in the queue c:\inetpub\mailroot\queue\, started it back up and it cleared it up. Immediately items that were stuck in the Queue folder started to get delivered Re: IIS SMTP email stuck in queue unable to send out. Basically, I selected SMTP from the IIS server node, entered credentials for my smtp server and saved it. Turns out, SMTP also had to be configured in IIS proper as well. SMTP was configured using the IIS6 manager. I recently ran into the same issue on server 2016.