SSRS report mail subsription is failing.

Question

Hi All,
I have one SSRS report which is deployed in my local report server. I need to activate email subscription for the same. I have given my outlook email address and SMTP server which is copied from outlook settings to Report configuration manager. Then I have
created a mail account and profile in sql server. I made the profile as public and default one. I have chosen basic authentication and provided my windows account and password for SMTP authentication. Port number is 25 which was given there as default.
SSL was not ticked. Then I have tried with the below sp.
EXEC msdb.dbo.sp_send_dbmail
@recipients='[email protected]'
 ,@subject='test'
,@body='test'
Everything worked fine. I have got the mail also. Then I tried to create a mail subscription for the deployed report on
my report server. I have scheduled it also. But I'm getting error message. Then searched in net and read somewhere that we are supposed to use windows authentication for SMTP. Then I changed the mail account to use windows authentication for SMTP. Even then
also I'm getting the same error given below.
Failure sending mail: The SMTP server requires a secure connection or the
client was not authenticated. The server response was: 5.7.1 Client was not
authenticatedMail will not be resent.
I have noticed another issue.
Because of the above error, I have chosen to use the secure connection (SSL) in the mail account. Also, SMTP authentication is Basic Authentication. I am not able to send email from database itself after checking the secure connection option. I
was able to send mail from database(by using the [proc dbo.sp_send_dbmail) when unchecking Secure connection option.  
I'm getting the below error when running this query
SELECT
*FROMmsdb.dbo.sysmail_event_logorderbylog_datedesc
The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 6 (2015-04-22T17:45:22). Exception Message: Cannot send mails to mail server. (The remote certificate is invalid according to the validation procedure.).
Please suggest
Regards,
Julie

Answer 1

See if this helps
https://saravananarumugam.wordpress.com/2012/04/30/the-smtp-server-requires-a-secure-connection-or-the-client-was-not-authenticated-the-server-response-was-5-7-1-client-was-not-authenticated/
Also check SSRS config
https://msdn.microsoft.com/en-us/library/ms345234.aspx
If still it doesnt work see if you can turn on anonymous authentication in SMTP server
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