I am routing outside mail through a smart hosts that has the following requirements:
port 465, SSL and authentication.
If I plug these settings in to outlook express, I can send test emails out without problems, but once I configure Send Connector on Exchange 2013 with the same settings, my emails get stuck in the outgoing queue with the following error message "Failed to connect. Winsock error code: 10051, Win32 error code: 10051, Error Message: A socket operation was attempted to an unreachable network"
Real smtp server name was masked for privacy with "smtp.outside.net"
Send Connector settings:
AddressSpaces : {SMTP:*;1}
AuthenticationCredential : System.Management.Automation.PSCredential
CloudServicesMailEnabled : False
Comment :
ConnectedDomains : {}
ConnectionInactivityTimeOut : 00:10:00
DNSRoutingEnabled : False
DomainSecureEnabled : False
Enabled : True
ErrorPolicies : Default
ForceHELO : False
Fqdn :
FrontendProxyEnabled : False
HomeMTA : Microsoft MTA
HomeMtaServerId : MAIL2013
Identity : Outside
IgnoreSTARTTLS : False
IsScopedConnector : False
IsSmtpConnector : True
MaxMessageSize : 25 MB (26,214,400 bytes)
Name : Outside
Port : 465
ProtocolLoggingLevel : Verbose
RequireOorg : False
RequireTLS : True
SmartHostAuthMechanism : BasicAuth
SmartHosts : {smtp.outside.net}
SmartHostsString : smtp.outside.net
SmtpMaxMessagesPerConnection : 20
SourceIPAddress : 0.0.0.0
SourceRoutingGroup : Exchange Routing Group (DWBGZMFD01QNBGN)
SourceTransportServers : {MAIL2013}
TlsAuthLevel :
TlsCertificateName :
TlsDomain :
UseExternalDNSServersEnabled : False