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Exchange 2010 Email Problems (intermittent)

exchange 2010
intermittent problems with email
when using to telnet to test to server; I get unrecognized command from EHLO; then I try a HELO and session timed out or connect to host lost
run several tests and get 18 second transaction time
all help is greatly appreciated!
delebute

SOLUTION

Chris H

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Alan Hardisty

Are you having inbound or outbound problems?

Rajitha Chimmani

Hope the telnet you tried is over port 25. If you dont specify a port it connects through port 23

David Elebute

ASKER

problem is with inbound messages and outbound for CC messages or even direct sends
we send email messages from our process server internal domain that the exchange server is but different subnets
server 192.168.200.7 process server 192.168.70.7 secure VPN between the two and process server has SMTP credentials domainname\username and password, tested working. username has send privileges
also our telnet tests are over port 25
delebute

David Elebute

ASKER

receive connector for process server enabled and in place
the only check is for anonymous connections; should I add windows authentication as well?
delebute

David Elebute

ASKER

we got a 5.3.3 unrecognized command when trying to send a simple EHLO. Using HELO instead caused the connection to time out
Further, when running an SMTP test from mxtoolbox.com, I get the following failures:

____________________________________________________________

220 ******************************************************************************22*****20*************0*00
Test Result
SMTP Reverse DNS Mismatch Warning - Reverse DNS does not match SMTP Banner More Info
SMTP TLS Warning - Does not support TLS. More Info
SMTP Transaction Time 18.439 seconds - Not good! on Transaction Time More Info
SMTP Banner Check OK - x.x.x.x resolves to x.x.x.x.nw.nuvox.net

SMTP Connection Time 0.733 seconds - Good on Connection time
SMTP Open Relay OK - Not an open relay.
Session Transcript:
Connecting to x.x.x.x

220 ******************************************************************************22*****20*************0*00 [671 ms]
EHLO MXTB-PWS3.mxtoolbox.com
500 5.3.3 Unrecognized command [5678 ms]
MAIL FROM: <supertool@mxtoolbox.com>
503 5.5.2 Send hello first [5678 ms]
RCPT TO: <test@example.com>
503 5.5.2 Send hello first [5678 ms]
QUIT
221 2.0.0 Service closing transmission channel [671 ms]
MXTB-PWS3v2 19328ms
All Help is Greatly Appreciated!

ASKER CERTIFIED SOLUTION

Alan Hardisty

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David Elebute

ASKER

set the no fixup protocol smtp 25 has been updated on our firewall
don't see any ESMTP INSPECTION section in our current configuration on the firewall
weird now getting the SMTP server requires secure connection or the client was not authenticated. the server response was: 5.7.1 Client was not authenticated error from our process server trying to send messages out to the team
thanks again Alan Hardisty
delebute

SOLUTION

Alan Hardisty

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David Elebute

ASKER

Here is the output

RunspaceId : 500b8dc7-1517-4ba4-82ab-7b346a68d483
AuthMechanism : Tls, Integrated, BasicAuth, BasicAuthRequireTLS, ExchangeServer
Banner :
BinaryMimeEnabled : True
Bindings : {192.168.200.7:25}
ChunkingEnabled : True
DefaultDomain :
DeliveryStatusNotificationEnabled : True
EightBitMimeEnabled : True
BareLinefeedRejectionEnabled : False
DomainSecureEnabled : False
EnhancedStatusCodesEnabled : True
LongAddressesEnabled : False
OrarEnabled : False
SuppressXAnonymousTls : False
AdvertiseClientSettings : False
Fqdn : server.domainname.local
Comment :
Enabled : True
ConnectionTimeout : 00:10:00
ConnectionInactivityTimeout : 00:05:00
MessageRateLimit : unlimited
MessageRateSource : IPAddress
MaxInboundConnection : 5000
MaxInboundConnectionPerSource : unlimited
MaxInboundConnectionPercentagePerSource : 100
MaxHeaderSize : 64 KB (65,536 bytes)
MaxHopCount : 60
MaxLocalHopCount : 12
MaxLogonFailures : 3
MaxMessageSize : 100 MB (104,857,600 bytes)
MaxProtocolErrors : 5
MaxRecipientsPerMessage : 5000
PermissionGroups : ExchangeUsers, ExchangeServers, ExchangeLegacyServers
PipeliningEnabled : True
ProtocolLoggingLevel : None
RemoteIPRanges : {50.192.142.230, 192.168.70.7, 192.168.200.2-192.168.200.255, 192.168.200.0-1
92.168.200.0}
RequireEHLODomain : False
RequireTLS : False
EnableAuthGSSAPI : False
ExtendedProtectionPolicy : None
LiveCredentialEnabled : False
TlsDomainCapabilities : {}
Server : SERVER
SizeEnabled : EnabledWithoutValue
TarpitInterval : 00:00:05
MaxAcknowledgementDelay : 00:00:30
AdminDisplayName :
ExchangeVersion : 0.1 (8.0.535.0)
Name : Default SERVER
DistinguishedName : CN=Default SERVER,CN=SMTP Receive Connectors,CN=Protocols,CN=SERVER,C
N=Servers,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrativ
e Groups,CN=DOMAINK,CN=Microsoft Exchange,CN=Services,CN=Configuration,D
C=DOMAIN,DC=local
Identity : SERVER\Default SERVER Guid : ce8146f6-68f0-4361-b63d-09beaaff0894
ObjectCategory : DOMAIN.local/Configuration/Schema/ms-Exch-Smtp-Receive-Connector
ObjectClass : {top, msExchSmtpReceiveConnector}
WhenChanged : 9/22/2014 5:55:45 PM
WhenCreated : 1/2/2014 7:41:26 PM
WhenChangedUTC : 9/22/2014 9:55:45 PM
WhenCreatedUTC : 1/3/2014 12:41:26 AM
OrganizationId :
OriginatingServer : server.domainname.local
IsValid : True

RunspaceId : 500b8dc7-1517-4ba4-82ab-7b346a68d483
AuthMechanism : BasicAuth
Banner :
BinaryMimeEnabled : True
Bindings : {127.0.0.1:25}
ChunkingEnabled : True
DefaultDomain :
DeliveryStatusNotificationEnabled : True
EightBitMimeEnabled : True
BareLinefeedRejectionEnabled : False
DomainSecureEnabled : False
EnhancedStatusCodesEnabled : True
LongAddressesEnabled : False
OrarEnabled : False
SuppressXAnonymousTls : False
AdvertiseClientSettings : False
Fqdn : server.domainname.local
Comment :
Enabled : True
ConnectionTimeout : 06:00:00
ConnectionInactivityTimeout : 00:05:00
MessageRateLimit : unlimited
MessageRateSource : IPAddress
MaxInboundConnection : 5000
MaxInboundConnectionPerSource : 20
MaxInboundConnectionPercentagePerSource : 2
MaxHeaderSize : 64 KB (65,536 bytes)
MaxHopCount : 60
MaxLocalHopCount : 12
MaxLogonFailures : 3
MaxMessageSize : 100 MB (104,857,600 bytes)
MaxProtocolErrors : 5
MaxRecipientsPerMessage : 200
PermissionGroups : AnonymousUsers, ExchangeUsers
PipeliningEnabled : True
ProtocolLoggingLevel : None
RemoteIPRanges : {127.0.0.1-127.0.0.1}
RequireEHLODomain : False
RequireTLS : False
EnableAuthGSSAPI : False
ExtendedProtectionPolicy : None
LiveCredentialEnabled : False
TlsDomainCapabilities : {}
Server : SERVER SizeEnabled : Enabled
TarpitInterval : 00:00:05
MaxAcknowledgementDelay : 00:00:30
AdminDisplayName :
ExchangeVersion : 0.1 (8.0.535.0)
Name : Windows SBS Fax Sharepoint Receive SERVER
DistinguishedName : CN=Windows SBS Fax Sharepoint Receive SERVER,CN=SMTP Receive Connectors,C
N=Protocols,CN=SERVER,CN=Servers,CN=Exchange Administrative Group (FYDIBO
HF23SPDLT),CN=Administrative Groups,CN=DOMAIN,CN=Microsoft Exchange,CN=
Services,CN=Configuration,DC=DOMAIN,DC=local
Identity : SERVER\Windows SBS Fax Sharepoint Receive SERVER
Guid : b1b8ffde-8bd2-43ab-8c56-6aca7a63c6be
ObjectCategory : DOMAIN.local/Configuration/Schema/ms-Exch-Smtp-Receive-Connector
ObjectClass : {top, msExchSmtpReceiveConnector}
WhenChanged : 1/26/2014 1:36:31 PM
WhenCreated : 1/2/2014 8:24:48 PM
WhenChangedUTC : 1/26/2014 6:36:31 PM
WhenCreatedUTC : 1/3/2014 1:24:48 AM
OrganizationId :
OriginatingServer : server.domainname.local
IsValid : True

RunspaceId : 500b8dc7-1517-4ba4-82ab-7b346a68d483
AuthMechanism : Tls
Banner :
BinaryMimeEnabled : True
Bindings : {192.168.200.7:25}
ChunkingEnabled : True
DefaultDomain :
DeliveryStatusNotificationEnabled : True
EightBitMimeEnabled : True
BareLinefeedRejectionEnabled : False
DomainSecureEnabled : False
EnhancedStatusCodesEnabled : True
LongAddressesEnabled : False
OrarEnabled : False
SuppressXAnonymousTls : False
AdvertiseClientSettings : False
Fqdn : remote.domianname.com
Comment :
Enabled : True
ConnectionTimeout : 00:10:00
ConnectionInactivityTimeout : 00:01:00
MessageRateLimit : unlimited
MessageRateSource : IPAddress
MaxInboundConnection : 5000
MaxInboundConnectionPerSource : 20
MaxInboundConnectionPercentagePerSource : 2
MaxHeaderSize : 64 KB (65,536 bytes)
MaxHopCount : 60
MaxLocalHopCount : 12
MaxLogonFailures : 3
MaxMessageSize : 100 MB (104,857,600 bytes)
MaxProtocolErrors : 5
MaxRecipientsPerMessage : 200
PermissionGroups : AnonymousUsers
PipeliningEnabled : True
ProtocolLoggingLevel : None
RemoteIPRanges : {192.168.201.0-255.255.255.255, 192.168.200.1-192.168.200.1, 0.0.0.0-192.168.
199.255}
RequireEHLODomain : False
RequireTLS : False
EnableAuthGSSAPI : False
ExtendedProtectionPolicy : None
LiveCredentialEnabled : False
TlsDomainCapabilities : {}
Server : SERVER
SizeEnabled : Enabled
TarpitInterval : 00:00:05
MaxAcknowledgementDelay : 00:00:30
AdminDisplayName :
ExchangeVersion : 0.1 (8.0.535.0)
Name : Windows SBS Internet Receive SERVER
DistinguishedName : CN=Windows SBS Internet Receive SERVER,CN=SMTP Receive Connectors,CN=Prot
ocols,CN=SERVER,CN=Servers,CN=Exchange Administrative Group (FYDIBOHF23SP
DLT),CN=Administrative Groups,CN=DOMAIN,CN=Microsoft Exchange,CN=Servic
es,CN=Configuration,DC=DOMAIN,DC=local
Identity : SERVER\Windows SBS Internet Receive SERVER
Guid : 69c2c5ee-1f47-4f65-8947-31b158711964
ObjectCategory : DOMAIN.local/Configuration/Schema/ms-Exch-Smtp-Receive-Connector
ObjectClass : {top, msExchSmtpReceiveConnector}
WhenChanged : 1/26/2014 1:35:49 PM
WhenCreated : 1/13/2014 12:31:30 PM
WhenChangedUTC : 1/26/2014 6:35:49 PM
WhenCreatedUTC : 1/13/2014 5:31:30 PM
OrganizationId :
OriginatingServer : server.domainname.local
IsValid : True

RunspaceId : 500b8dc7-1517-4ba4-82ab-7b346a68d483
AuthMechanism : Tls
Banner :
BinaryMimeEnabled : True
Bindings : {192.168.70.7:25, 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 : processserver.domain.local
Comment :
Enabled : True
ConnectionTimeout : 00:10:00
ConnectionInactivityTimeout : 00:05:00
MessageRateLimit : unlimited
MessageRateSource : IPAddress
MaxInboundConnection : 5000
MaxInboundConnectionPerSource : 20
MaxInboundConnectionPercentagePerSource : 2
MaxHeaderSize : 64 KB (65,536 bytes)
MaxHopCount : 60
MaxLocalHopCount : 12
MaxLogonFailures : 3
MaxMessageSize : 100 MB (104,857,600 bytes)
MaxProtocolErrors : 5
MaxRecipientsPerMessage : 200
PermissionGroups : AnonymousUsers
PipeliningEnabled : True
ProtocolLoggingLevel : Verbose
RemoteIPRanges : {50.192.142.230, 0.0.0.0-255.255.255.255}
RequireEHLODomain : False
RequireTLS : False
EnableAuthGSSAPI : False
ExtendedProtectionPolicy : None
LiveCredentialEnabled : False
TlsDomainCapabilities : {}
Server : SERVER
SizeEnabled : Enabled
TarpitInterval : 00:00:05
MaxAcknowledgementDelay : 00:00:30
AdminDisplayName :
ExchangeVersion : 0.1 (8.0.535.0)
Name : process_srvr
DistinguishedName : CN=process_srvr,CN=SMTP Receive Connectors,CN=Protocols,CN=SERVER,CN=Servers,C
N=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN
=DOMAIN,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=DOMAIN,DC=local
Identity : SERVER\process_srvr
Guid : f0b37af0-6a03-439b-b588-8d2fd864db3a
ObjectCategory : DOMAIN.local/Configuration/Schema/ms-Exch-Smtp-Receive-Connector
ObjectClass : {top, msExchSmtpReceiveConnector}
WhenChanged : 9/22/2014 5:56:10 PM
WhenCreated : 8/1/2014 6:42:30 PM
WhenChangedUTC : 9/22/2014 9:56:10 PM
WhenCreatedUTC : 8/1/2014 10:42:30 PM
OrganizationId :
OriginatingServer : server.domainname.local
IsValid : True

David Elebute

ASKER

so far not seeing any failures on our process server since fixup protocol change made, but now not getting any email delivery coming from process server!
how can we check smtp mail path?
delebute

SOLUTION

Alan Hardisty

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David Elebute

ASKER

thank you for all the help!
it is greatly appreciated
delebute