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I asked this question on Stack Overflow and I was advised to come here. I do not normally deal with these kind of issues myself.

I have a scheduled job running in SQL Server 2008, but I have a problem with sending emails.

I get the error message;

The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 1 (2013-04-11T10:05:12). Exception Message: Cannot send mails to mail server. (The operation has timed out.). Sending Mail using Account 1 (2013-04-11T10:06:53). Exception Message: Cannot send mails to mail server. (Failure sending mail.). )

Also in the error log I get messages like; 

04/10/2013 14:03:51,,Error,3617,The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 1 (2013-04-10T14:02:10). Exception Message: Cannot send mails to mail server. (Mailbox unavailable. The server response was: 5.7.1 Client does not have permissions to send as this sender).

In the event log I get the following message;

Exception Type: Microsoft.Sql.Server.Management.SqlMail.Server.Common.BaseException Message: There was an error on the connection. Reason: Timeout expired. The timeout period elapsed prior to obtaining a connection from the pool. This may have occurred because all pooled connections were in use and max pool size was reached.

How do I fix this?

arame3333
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    Punch "Client does not have permissions to send as this sender" into your favorite search engine. – David Schwartz Apr 12 '13 at 08:31
  • Is this server trying to send mail out from an Exchange server or something? If so, I would take a look at the send connectors on the Exchange side to see that this IP is allowed to relay. – jmreicha Apr 12 '13 at 15:11

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