Windows IIS SMTP server internal spoofing

Hi,
I setup windows IIS based smtp server, I had below requirements.
1. all application emails should be relayed internally and externally,from domain and non-domain (Windows & Unix systems)
2. Only list of email domains (we have close to 20 email domain)should be able to send emails to this SMTP virtual server
3. Internal email spoofing should not be allowed
4. this system should not accept email from domains other than specified domains (Point 2).
I verified all settings, now I am able to send email internally & externally but my problem is, its accepting emails from any domain (Other than domain we use) and spoofing also.
Thanks!
Karthikeyan
Thanks, Karthikeyan R

More if you ask them here: http://forums.iis.net/
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FTP error 426 with Windows IIS server

Dear SAP,
We are experiencing an issue between SAP PI 7.0 SP15 on P-Series AIX IBM Server and the Windows IIS FTP server. The interface in PI does connect to 3 systems with the FTP file adapter (a Mainframe, an AS400 and a Windows IIS FTP server). The mainframe and the AS400 connection are working fine but for the IIS we are getting a FTP failure in 90% of the transfers in 10% it works. With other clients (also one based on JFTP) everything works fine with the IIS server. The files are only 2kb and not to large as described in the File Adapter FAQ note.
There where tests with active (FTP failure 500) and passive connections, the timeout value was increased on both sides. The connection bandwidth reached never more than 40% and there were always enough CPU processes available on both sides.
Following technical details for the passive connection failure:
XI we do get following error log in MDT
2008-09-09 20:27:01     Success     Connecting to FTP server "bla.com"
2008-09-09 20:27:02     Success     Write to FTP server "bla.com", directory "/sapedi/Outbound/856otest", -> file "SAPASN253201157.txt"
2008-09-09 20:27:02     Success     Transfer: "TXT" mode, size 2131 bytes, character encoding ISO8859-1
2008-09-09 20:27:02     Error     Attempt to process file failed with com.sap.aii.adapter.file.ftp.FTPEx: 426 Connection closed; transfer aborted.
2008-09-09 20:27:02     Error     MP: Exception caught with cause com.sap.aii.af.ra.ms.api.RecoverableException: Connection closed; transfer aborted.: com.sap.aii.adapter.file.ftp.FTPEx: 426 Connection closed; transfer aborted.
2008-09-09 20:27:02     Error     Exception caught by adapter framework: Connection closed; transfer aborted.
The log of XI from /usr/sap/PXQ/DVEBMGS00/j2ee/cluster/server0/log/applications/com.sap.xi/xi.2.log
0#Error#1#com.sap.aii.adapter.file.util.AuditLog#Plain###FILE_ERR_211#
xi.2.log:#1.#3A2BF0015004006F0000098D00096046000456F11A40B559#1221493434398#/Applications/ExchangeInfrastructure/AdapterFramework/Services/ADAPTER/ADMIN/File#sap.com/com.sap.aii.af.app#com.sap.aii.adapter.file.XI2File.processMessage(Message)#J2EE_GUEST#0#SAP J2EE Engine JTA Transaction : [03affffff863a005363]#n/a##de1f90f0833c11dda1993a2bf0015004#XI XI2File[CC_FILE_CPS_PRC316_IN/LEG_CPSQ_BS/]_104767##0#0#Error#1#com.sap.aii.adapter.file.XI2File#Plain###File processing failed with com.sap.aii.adapter.file.ftp.FTPEx: 426 Connection closed; transfer aborted.#
xi.2.log:#1.#3A2BF0015004006F0000098F00096046000456F11A40B6AB#1221493434398#/Applications/ExchangeInfrastructure/AdapterFramework/Services/ADAPTER/ADMIN/File#sap.com/com.sap.aii.af.app#com.sap.aii.adapter.file.util.AuditLog.addAuditLog(PublicMessageKey, String, AuditLogStatus, String, String, Object[])#J2EE_GUEST#0#SAP J2EE Engine JTA Transaction : [03affffff863a005363]#n/a##de1f90f0833c11dda1993a2bf0015004#XI XI2File[CC_FILE_CPS_PRC316_IN/LEG_CPSQ_BS/]_104767##0#0#Error#1#com.sap.aii.adapter.file.util.AuditLog#Plain###FILE_ERR_211#
xi.2.log:#1.#3A2BF0015004006B000009CB00096046000456F11ABB9521#1221493442450#/Applications/ExchangeInfrastructure/AdapterFramework/Services/ADAPTER/ADMIN/File#sap.com/com.sap.aii.af.app#com.sap.aii.adapter.file.XI2File.processMessage(Message)#J2EE_GUEST#0#SAP J2EE Engine JTA Transaction : [03affffff863a005364]#n/a##1e2afb80833d11ddc03c3a2bf0015004#XI XI2File[CC_FILE_CPS_PRC316_IN/LEG_CPSQ_BS/]_104771##0#0#Error#1#com.sap.aii.adapter.file.XI2File#Plain###File processing failed with com.sap.aii.adapter.file.ftp.FTPEx: 426 Connection closed; transfer aborted.#
xi.2.log:#1.#3A2BF0015004006B000009CD00096046000456F11ABB966E#1221493442451#/Applications/ExchangeInfrastructure/AdapterFramework/Services/ADAPTER/ADMIN/File#sap.com/com.sap.aii.af.app#com.sap.aii.adapter.file.util.AuditLog.addAuditLog(PublicMessageKey, String, AuditLogStatus, String, String, Object[])#J2EE_GUEST#0#SAP J2EE Engine JTA Transaction : [03affffff863a005364]#n/a##1e2afb80833d11ddc03c3a2bf0015004#XI XI2File[CC_FILE_CPS_PRC316_IN/LEG_CPSQ_BS/]_104771##0#0#Error#1#com.sap.aii.adapter.file.util.AuditLog#Plain###FILE_ERR_211#
On the IIS server side we have the following log for the failure:
2008-09-10 08:32:50 x.x.x.20 SAPEDI MSFTPSVC1 BLA x.x.x.x 21 [68977]USER SAPEDI - 331 0 0 0 0 FTP - - - -
2008-09-10 08:32:50 x.x.x.20 SAPEDI MSFTPSVC1 BLA x.x.x.x 21 [68977]PASS - - 230 0 0 0 0 FTP - - - -
2008-09-10 08:32:50 x.x.x.20 SAPEDI MSFTPSVC1 BLA x.x.x.x 21 [68977]CWD /sapedi/Outbound/856otest - 250 0 0 0 0 FTP - - - -
2008-09-10 08:32:50 x.x.x.20 SAPEDI MSFTPSVC1 BLA x.x.x.x 21 [68977]created SAPASN253201157.txt - 426 995 0 0 16 FTP - - - -
2008-09-10 08:32:50 x.x.x.20 SAPEDI MSFTPSVC1 BLA x.x.X.X 21 [68977]QUIT - - 426 0 0 0 0 FTP - - - -
Thank you for your help.
Edited by: PhilippJ on Sep 17, 2008 3:36 PM

Hi,
Better to check with Basis & network team, they will sort out easily

PI FTP error 426 during Windows IIS connection

Hi,
We are experiencing an issue between SAP PI 7.0 SP15 on P-Series AIX IBM Server and the Windows IIS FTP server. The interface in PI does connect to 3 systems with the FTP file adapter (a Mainframe, an AS400 and a Windows IIS FTP server). The mainframe and the AS400 connection are working fine but for the IIS we are getting a FTP failure in 90% of the transfers in 10% it works. With other clients (also one based on JFTP) everything works fine with the IIS server. The files are only 2kb and not to large as described in the File Adapter FAQ note.
There where tests with active (FTP failure 500) and passive connections, the timeout value was increased on both sides. The connection bandwidth reached never more than 40% and there were always enough CPU processes available on both sides.
Following technical details for the passive connection failure:
XI we do get following error log in MDT
2008-09-09 20:27:01 Success Connecting to FTP server "bla.com"
2008-09-09 20:27:02 Success Write to FTP server "bla.com", directory "/sapedi/Outbound/856otest", -> file "SAPASN253201157.txt"
2008-09-09 20:27:02 Success Transfer: "TXT" mode, size 2131 bytes, character encoding ISO8859-1
2008-09-09 20:27:02 Error Attempt to process file failed with com.sap.aii.adapter.file.ftp.FTPEx: 426 Connection closed; transfer aborted.
2008-09-09 20:27:02 Error MP: Exception caught with cause com.sap.aii.af.ra.ms.api.RecoverableException: Connection closed; transfer aborted.: com.sap.aii.adapter.file.ftp.FTPEx: 426 Connection closed; transfer aborted.
2008-09-09 20:27:02 Error Exception caught by adapter framework: Connection closed; transfer aborted.
The log of XI from /usr/sap/PXQ/DVEBMGS00/j2ee/cluster/server0/log/applications/com.sap.xi/xi.2.log
0#Error#1#com.sap.aii.adapter.file.util.AuditLog#Plain###FILE_ERR_211#
xi.2.log:#1.#3A2BF0015004006F0000098D00096046000456F11A40B559#1221493434398#/Applications/ExchangeInfrastructure/AdapterFramework/Services/ADAPTER/ADMIN/File#sap.com/com.sap.aii.af.app#com.sap.aii.adapter.file.XI2File.processMessage(Message)#J2EE_GUEST#0#SAP J2EE Engine JTA Transaction : 03affffff863a005363#n/a##de1f90f0833c11dda1993a2bf0015004#XI XI2FileCC_FILE_CPS_PRC316_IN/LEG_CPSQ_BS/_104767##0#0#Error#1#com.sap.aii.adapter.file.XI2File#Plain###File processing failed with com.sap.aii.adapter.file.ftp.FTPEx: 426 Connection closed; transfer aborted.#
xi.2.log:#1.#3A2BF0015004006F0000098F00096046000456F11A40B6AB#1221493434398#/Applications/ExchangeInfrastructure/AdapterFramework/Services/ADAPTER/ADMIN/File#sap.com/com.sap.aii.af.app#com.sap.aii.adapter.file.util.AuditLog.addAuditLog(PublicMessageKey, String, AuditLogStatus, String, String, Object[])#J2EE_GUEST#0#SAP J2EE Engine JTA Transaction : 03affffff863a005363#n/a##de1f90f0833c11dda1993a2bf0015004#XI XI2FileCC_FILE_CPS_PRC316_IN/LEG_CPSQ_BS/_104767##0#0#Error#1#com.sap.aii.adapter.file.util.AuditLog#Plain###FILE_ERR_211#
xi.2.log:#1.#3A2BF0015004006B000009CB00096046000456F11ABB9521#1221493442450#/Applications/ExchangeInfrastructure/AdapterFramework/Services/ADAPTER/ADMIN/File#sap.com/com.sap.aii.af.app#com.sap.aii.adapter.file.XI2File.processMessage(Message)#J2EE_GUEST#0#SAP J2EE Engine JTA Transaction : 03affffff863a005364#n/a##1e2afb80833d11ddc03c3a2bf0015004#XI XI2FileCC_FILE_CPS_PRC316_IN/LEG_CPSQ_BS/_104771##0#0#Error#1#com.sap.aii.adapter.file.XI2File#Plain###File processing failed with com.sap.aii.adapter.file.ftp.FTPEx: 426 Connection closed; transfer aborted.#
xi.2.log:#1.#3A2BF0015004006B000009CD00096046000456F11ABB966E#1221493442451#/Applications/ExchangeInfrastructure/AdapterFramework/Services/ADAPTER/ADMIN/File#sap.com/com.sap.aii.af.app#com.sap.aii.adapter.file.util.AuditLog.addAuditLog(PublicMessageKey, String, AuditLogStatus, String, String, Object[])#J2EE_GUEST#0#SAP J2EE Engine JTA Transaction : 03affffff863a005364#n/a##1e2afb80833d11ddc03c3a2bf0015004#XI XI2FileCC_FILE_CPS_PRC316_IN/LEG_CPSQ_BS/_104771##0#0#Error#1#com.sap.aii.adapter.file.util.AuditLog#Plain###FILE_ERR_211#
On the IIS server side we have the following log for the failure:
2008-09-10 08:32:50 x.x.x.20 SAPEDI MSFTPSVC1 BLA x.x.x.x 21 68977USER SAPEDI - 331 0 0 0 0 FTP - - - -
2008-09-10 08:32:50 x.x.x.20 SAPEDI MSFTPSVC1 BLA x.x.x.x 21 68977PASS - - 230 0 0 0 0 FTP - - - -
2008-09-10 08:32:50 x.x.x.20 SAPEDI MSFTPSVC1 BLA x.x.x.x 21 68977CWD /sapedi/Outbound/856otest - 250 0 0 0 0 FTP - - - -
2008-09-10 08:32:50 x.x.x.20 SAPEDI MSFTPSVC1 BLA x.x.x.x 21 68977created SAPASN253201157.txt - 426 995 0 0 16 FTP - - - -
2008-09-10 08:32:50 x.x.x.20 SAPEDI MSFTPSVC1 BLA x.x.X.X 21 68977QUIT - - 426 0 0 0 0 FTP - - - -
Thank you for your help.

No this was not solved, we went for another FTP solutions (GlobeScape) and it just worked fine with it.

Setting SMTP Server for POP Acct in Mail

I can't seem to set the smtp server properly in an account for my personal (cf business) email -- this one's a pop server. I keep getting a rejection message, and the smtp server line in the setup window reads something like "server offline." My business email (Exchange) works fine.
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Did you happen remove that account then recreate it?
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550 5.7.1 NDR's as mail volume from IIS Virtual SMTP server to Exchange 2010 increases

We have a virtual win 2008 server that has a Virtual SMTP server running via IIS. A separate application on this server drops emails in the pickup directory to forward to our Exchange 2010 environment and this works fine. The odd issue is that as the volume
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550 5.7.1 Anonymous clients does not have permissions to send as this sender
As soon as we throttle this application the issue stops. And the same emails that bounced can be resubmitted with no issues
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RunspaceId
: 1e06e317-da65-4916-9b2c-e1253b4b550b
AuthMechanism                          : None
Banner                                  :
BinaryMimeEnabled
: True
Bindings
                 : {0.0.0.0:25}
ChunkingEnabled
   : True
DefaultDomain
DeliveryStatusNotificationEnabled
: True
EightBitMimeEnabled
: True
BareLinefeedRejectionEnabled
: False
DomainSecureEnabled
: False
EnhancedStatusCodesEnabled
: True
LongAddressesEnabled
: False
OrarEnabled
    : False
SuppressXAnonymousTls                   : False
AdvertiseClientSettings
: False
Fqdn
                : HT02.corp.com
Comment                                 :
Enabled                                 : True
ConnectionTimeout                      : 00:10:00
ConnectionInactivityTimeout
: 00:05:00
MessageRateLimit                        : unlimited
MessageRateSource                       : IPAddress
MaxInboundConnection
: 5000
MaxInboundConnectionPerSource
: 100
MaxInboundConnectionPercentagePerSource : 100
MaxHeaderSize
         : 64 KB (65,536 bytes)
MaxHopCount                            : 60
MaxLocalHopCount
: 8
MaxLogonFailures                       : 3
MaxMessageSize
     : 30 MB (31,457,280 bytes)
MaxProtocolErrors
           : 5
MaxRecipientsPerMessage
: 200
PermissionGroups                        : AnonymousUsers
PipeliningEnabled
: True
ProtocolLoggingLevel
: Verbose
RemoteIPRanges                          : REDACTED
RequireEHLODomain
: False
RequireTLS                              : False
EnableAuthGSSAPI
       : False
ExtendedProtectionPolicy
: None
LiveCredentialEnabled
: False
TlsDomainCapabilities
Server                                  : HT02
SizeEnabled
       : EnabledWithoutValue
TarpitInterval                          : 00:00:05
MaxAcknowledgementDelay
: 00:00:30
AdminDisplayName
ExchangeVersion
              : 0.1 (8.0.535.0)
Name
               : Internal Relay
DistinguishedName                      : REDACTED
Identity
          : HT02\Internal Relay
Guid
: a1f5af2e-6d53-4cb9-80b6-d19aab6879b4
ObjectCategory
        : REDACTED
ObjectClass                             : {top,msExchSmtpReceiveConnector}
WhenChanged
        : 6/20/2014 11:12:17 AM
WhenCreated
        : 2/18/2011 10:15:58 AM
WhenChangedUTC
       : 6/20/2014 3:12:17 PM
WhenCreatedUTC
         : 2/18/2011 3:15:58 PM
OrganizationId
OriginatingServer                       : dc04.corp.com
IsValid
: True

Just to clarify, this is not a pickup directory on an Exchange server but on a Windows 2008 server running an SMTP Virtual server in IIS 6.0. The problem happens only when the message volume from this server to Exchange increases to over ~500 messages a
minute. When that happens the messages get bounced from Exchange with the following info in the NDR
550 5.7.1 Anonymous clients does not have permissions to send as this sender
If we resubmit all the bounce messages at a lower volume per minute we do not see the issue. I'm still working on replicating the issue now that we have logging turned up on the receive connectors.
In addition some messages are being bounced with the following NDR message
554 5.6.0 Invalid message content
These messages are always between 65-70KB and have around 200 recipients
In the Exchange receive logs for the receive connector for these messages we see the following message (with different sizing)
A parsing error has occurred:MIME content error:
Singletext value size
(32781)exceeded allowed maximum
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SMTP Server Windows Azure Cloud

Hello everyone,
Currently intern at a BI company, I must implement a decision-making on a VM Windows Azure Cloud.
Since few days I am facing a problem.
I must implement an automatic email sending in the case of an error.
To do this, I need to specify an SMTP server.
When I'm local (on my machine), I have no problem, I use the SMTP server used my company.
Of course, the SMTP server of the company does not work in the Cloud.
Can you clarify me about this if you have some answers ?
Thank you in advance,
Best regards,
Vivien

One suggestion may be to create a VPN between Azure and your environment, and use your local SMTP server for this.
-kn
Kristian (Virtualization and some coffee: http://kristiannese.blogspot.com )

Windows 2008 R2 smtp server Relay only selected servers without authentication

Hello,
Need help in configuring Windows SMTP server.
Windows 2008 R2 Server. SMTP service is installed and configured.
Access TAB -- Authentication TAB -- Anonymous Access is selected..
Relay TAB -- Only the list below is selected and specfic scanners and application servers IPs are mentioned.
Issue: Even though we have specified list of IPs to relay from this server, Anybody can send mails using this server ( open Relay )
-- My requirement is to relay specific IPs of scanners and App servers without any authentication, can anybody help me configure windows smtp server to achieve my requirements.
Any help will be highly appreciated.
Regards,
Ghouse

Hi,
I recommend you refer to the following article to configure the smtp server:
Setup and Configure SMTP Server on Windows Server 2008 R2
In addition, you should ask this in Windows server forum as this is not an exchange problem:
http://social.technet.microsoft.com/Forums/en-US/home?forum=windowsserver2008r2webtechnologies
Thanks.
Niko Cheng
TechNet Community Support

Dreamweaver (on Windows 7) wont connect to IIS (v7) Server using "FTP over SSL/TLS..."

I am evauating wether to purchase Dreamweaver CS6...
Dreamweaver CS6 trial (on Windows 7) wont connect to IIS (v7) Server using "FTP over SSL/TLS (explicit encryption)". I have a NEW Godaddy SSL certificate installed on the IIS server.
On connecting Dreamweaver states: "Server Certificate has expired or contains invalid data"
I have tried:
-ALL the Dreamweaver Server setup options
-Using multiple certificates (tried 2048 bit and 4096 bit Godaddy SSL certificates)
-Made sure the certificate 'issued to' domain name matches my domain name.
I am able to connect no problem using Filezilla, with equivalent Filezilla setting "Require explicit FTP over TLS". I can also connect fine using Microsoft Expression web.

Thanks for your prompt reply.
My comments:
1) You should update your tread (forums.adobe.com/thread/889530) to reflect that it still occurs on CS6 (I had already read it but figured it was an old tread and thus should be fixed by now).
2) You said “These warnings will also pop up for your users if you have a store saying the SSL certificate does not match the domain/ip and this can make users checking out in a storefront very nervous” . This does not seem to be correct – my https pages display properly using the same Godaddy certificate … using IE:
3) Godaddy is not my host (I use Amazon AWS) – but the SSL certificate is from them.

SMTP server on WIndows 7

Hi All,
In one of my application, I want to send Email out. I am using Windows 7 on my development machine, but I am getting below error
A message sent to adapter "SMTP" on send port "SendPortEmail" with URI "[email protected]" is suspended.
Error details: The transport failed to connect to the server.
Not sure if I can implement SMTP server functionality on Windows 7 after reading this http://stackoverflow.com/questions/8041856/smtp-local-server-in-windows-7-running-iis7.
Can you guys please suggest me whether it is possible or not. If yes please suggest the way do so.
Thanks, Girish R. Patil.

Hi All,
Thanks for all your inputs.
I have implemented the solution suggested by you.
Right now, I have used smtp4dev. By using this my mail is getting created and sent from biztalk. I think smtp4dev is working as simulator, as it is not sending the mail to the mentioned email address. It just accepts the mail information from biztalk and
generates below mail:
So, looks like this occurs through simulation as the recipient mentioned in this did not get mail.
After all this, I am still getting following Warning in event log.
Thanks, Girish R. Patil.

ICloud SMTP server not working on Windows Live

I can use iCloud to read and send messages on my iPhones and using the web interface in Safari but it doesn't seem to work with Windows Live Mail.
I'm using the following settings:
IMAP (Incoming Mail Server) information:
Server name: imap.mail.me.com
SSL Required: Yes
Port: 993
Username: [email protected] (use your @me.com address from your iCloud account)
Password: Your iCloud password
SMTP (outgoing mail server) information:
Server name: smtp.mail.me.com
SSL Required: Yes
Port: 587
SMTP Authentication Required: Yes
Username: [email protected] (use your @me.com address from your iCloud account)
Password: Your iCloud password
I can read messages in Windows Live but I can't send. I get an error and if I click "Send/Receive", I get a window that pops up with my account username and password. When I retype that it just keeps popping up until I hit cancel. It's like the server is not responding at all.
Please help.

Click on “Settings”
Choose “Accounts & Sync”
Select “Add Acount”
You’ll be presented with a list of Email accounts. Choose “Email”
Type in your email “[email protected]” and enter your iCloud password
I suggest changing your iCloud password to be the same as your iCloud email password. It just makes things easier
Under incoming settings enter the following
“imap.mail.me.com”
Port should be “993″
Security type “SSL/TLS”
Outgoing settings under SMTP server type in “smtp.me.com”
Under Port type in “587″
Security type, select “No”
“Require Sign-in”
Enter your iCloud username and password.

Messages queueing usng IIS SMTP Relay server for Office 365

We have SMTP relay server in IIS for office 365. We followed the setup provided by Microsoft but messages are stuck inside the queue folder.
Any help?

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:\InetPub\MailRoot\BadMail folder.
In addition, since it is related to IIS, you can also ask in IIS forum below for professional assistance:
http://forums.iis.net/
Best regards,
Susie

Fixing the SMTP server of localhost

I have installed the role of the SMTP server in my VPS and it's okay as you see there is a red mark on.
screenshot : prntscr .com/46tup6
(remove the space in the link between the "r" and ".", my account is not verified to post links) i want to fix this problem and need tomake the SMTP working normal.
I think only can you can help me fix this hope you answer me soon!
Thanks,

Hi MalikMax,
Did you confirm your SMTP configuration completed? You can refer the following related third party article to complete your configuration first.
How to set up an Internal SMTP Service for Windows Server 2012 Essentials
http://blog.powerbiz.net.au/exchange/how-to-set-up-an-internal-smtp-service-for-windows-server-2012-essentials/
More about the IIS question please post to the IIS forum.
IIS support forum
http://forums.iis.net/
Thanks for your understanding and support
Hope this helps.
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Mail to blocked SMTP server stalls mails to other SMTP servers

Hi,
I have a particularly weird problem.
In Mail.app I have a Mobile Me account, a personal IMAP account and an Exchange account (working over IMAP etc. as it's Exchange server 2003 so I don't get all the fruity Snow Leopard/Exchange goodness).
The problem I have is this- in the office they block access to external SMTP servers (quite rightly).
If I send a mail through my Mobile Me or personal IMAP account and forget to tell it to use the internal work SMTP server then Mail.app will sit forever trying to connect to the external SMTP server and never time out (or if it does timeout it must be more than a few hours).
This isn't a huge problem in and of itself. However from this point on any mail I send will sit behind the stalled e-mail in the queue and never go out- so even my internal mails hang around not sending.
The only indication of this is the non-stop spinning wheel on the sent items folder and the never-ending 'Connecting to smtp.me.com' in the activity window.
The only way to resolve this is to go to the activity window and cancel all connections to the offending SMTP server. At that point the 'Outbox' folder will appear in my folder list and show me all of the e-mails it hasn't sent. I then have to open each one individually and click send again, at which point they go out (provided they still have the correct internal SMTP server selected).

Ernie,
Thanks for the response. I have previously seen Mail.app fail to send and bring the message back up telling me this- but that usually happens quite some time after trying to send, if at all, and I don't recall ever having this error happen in the office (where they are blocking these ports).
I have had similar issues when travelling and trying to send through hotel networks that typically block port 25- even then I rarely get a failure message (note that this has been happening both on 10.5.x and my clean install of 10.6.x)
I did check to see if the network here was doing some spoofing on SMTP ports but it isn't;
#####:~ #####$ time telnet smtp.me.com 25
Trying 17.148.16.31...
telnet: connect to address 17.148.16.31: Operation timed out
telnet: Unable to connect to remote host
real 1m15.019s
user 0m0.002s
sys 0m0.003s
I get the same 1m15s timeout on port 465 & 587, yet Mail.app never seems to give up trying.
I tried sending to an external SMTP server without SSL to see if the behaviour was any different- but after 15 mins it's still trying so I guess not.
Weird.

Windows IIS SMTP server internal spoofing

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