Unable to send email from SharePoint

You have configured your SharePoint Outgoing Email but even the configuration correct you could not able to send emails from SharePoint.
For more information about how to configure outgoing emails on SharePoint please check following article:
http://technet.microsoft.com/en-us/library/cc263462.aspx

So what you can do;

First Check the ULS Logs ; You may facing following error;

Failed attempt 1 sending mail to recipients: bugra@contoso.com . Mail Subject: System Account has invited you “Blog Members”.
Error: SmtpException while sending
email: System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.1
Client was not authenticated
at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode,
String response)     at
System.Net.Mail.SmtpTransport.SendMail(MailAddress sender,
MailAddressCollection recipients, String deliveryNotify, Boolean allowUnicode,
SmtpFailedRecipientException&

 

Usually this problem not caused by SharePoint it self, It is happening when SharePoint connects to Exchange server but Exchange is not authorize SharePoint to send emails. Why ? Because by design SharePoint use anonymous authentication to connect Exchange and OOB you can not configure SharePoint for any other authentication for using SMTP emails . If the recieve connector of the Exchange will require authentication that would be the problem .

You can test your stmp server by telnet client for anonymous authentication. or may collect Network Monitor logs that what is the communication and what is the authentication when SharePoint is trying to send emails.

For Telnet test;
1) Start a command prompt with administrator priviledges.
2) type following command:
telnet <Your SMTP server IP> 25
type EHLO

250-SIZE 15360000
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH NTLM ***** Server requires NTLM .
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250-XEXCH50
250 XSHADOW

 

In network trace you can detect as

Frame: Number = 1087, Captured Frame Length = 316, MediaType = ETHERNET
+ Ethernet: Etype = Internet IP (IPv4),DestinationAddress:[00-50-56-B3-16-5A],SourceAddress:[38-22-D6-D4-49-80]
+ Ipv4: Src = 10.10.100.20, Dest = 10.20.100.59, Next Protocol = TCP, Packet ID = 9437, Total IP Length = 302
+ Tcp: Flags=…AP…, SrcPort=SMTP(25), DstPort=46805, PayloadLen=262, Seq=41429760 – 41430022, Ack=1350847993, Win=256 (scale factor 0x8) = 65536
– Smtp: Rsp 250 -<server> Hello [10.20.100.59], 262 bytes
– Response: 250 -<server> Hello [10.20.100.59]
ReplyCode: 250, OK, queuing for node node started, or Requested mail action okay, completed
+ ReplyMessage: -<server>  Hello [10.20.100.59] —-> Sharepoint opens session with 10.20.100.59
ReplyMessage: 250-SIZE
ReplyMessage: 250-PIPELINING
ReplyMessage: 250-DSN
ReplyMessage: 250-ENHANCEDSTATUSCODES
ReplyMessage: 250-STARTTLS
ReplyMessage: 250-X-ANONYMOUSTLS
ReplyMessage: 250-AUTH NTLM —-> Exchange providing NTLM.
     ReplyMessage: 250-X-EXPS GSSAPI NTLM
ReplyMessage: 250-8BITMIME
ReplyMessage: 250-BINARYMIME
ReplyMessage: 250-CHUNKING
ReplyMessage: 250-XEXCH50
ReplyMessage: 250-XRDST
ReplyMessage: 250 XSHADOW

For Resolution:
You can
1) Giving SharePoint Computer account mail submit priviledges
2) Creating a new Recieve Connector on Exchange for SharePoint and provide only anonymous auth.

 

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Moss 2007 – Troubleshooting incoming email problems

Windows SharePoint Services 3.0 uses e-mail handlers to route incoming e-mail from virtually any e-mail client to a list in your SharePoint site. Each e-mail-enabled list is associated with a unique e-mail address, and each e-mail handler is associated with a particular list type.

For troubleshooting incoming e-mails

1) Check Central Administration ->  Operations -> Incoming E-Mail Settings  is correctly configured.

2) Check your library – Settings-> Incoming E-mail settings is correctly configured.

If you correctly enable Incoming emails settings, you should have also an installed smtp server feature (for Windows server 2008 r2)
At this point i want to tell about the process of an incoming email distribution. When you send an email to a sharepoint list first your mail is delivered by your mail server and pass through the your sharepoint machine smtp server. It stored c:\inetpub\mailroot\drop folder with a file format of eml. The timer job of “Windows SharePoint Services Incoming E-Mail” is monitoring your mailroot\drop folder and when it find an email it process this mail and deliver the attachments to destination document library.

3) Check your Mailroot/drop folders stores eml files.

Incoming e-mail uses the Microsoft SharePoint Directory Management Service to connect SharePoint sites to the directory services used by your organization. If you enable the Microsoft SharePoint Directory Management Service, users can create and manage distribution groups from SharePoint sites. SharePoint lists that use e-mail can then be found in directory services, such as the Address Book. You must also select which distribution group requests from SharePoint lists require approval. The Microsoft SharePoint Directory Management Service can be installed on a server in the farm, or you can use a remote Microsoft SharePoint Directory Management Service.

4) If you are using Microsoft SharePoint Directory Management Service  Check Microsoft SharePoint Directory Management Service is running.

5) Check your sharepoint timer service identity has correct rights on mailroot folders. (you can check it from services.msc)

6) Trace the log messages using ULSViewer program with a filter of “category equals E-Mail”

For more information of Configuring Incoming E-Mail Settings:
http://technet.microsoft.com/en-us/library/cc287879(office.12).aspx