Exchange 2019 Send Connector not working

Hi leop,
Are you getting any bounce back when you send email after configuring send connector?
If yes please post the error.

Do you have a firewall. If yes do you have SMTP inspection enabled in the firewall.

The Scoping of the Send Connector is set to Domain=*?

it looks like bounce back points to security errors

outside@gmail.com (outside@gmail.com)
Your message wasn't delivered due to a permission or security issue. It may have been rejected by a moderator, the address may only accept email from certain senders, or another restriction may be preventing delivery.

The following organization rejected your message: smarthost@mhydmain.com.






Diagnostic information for administrators:
Generating server: exch2019.mydomain.com
outside@gmail.com
my-smarthost.mydomain..com
Remote Server returned '550 5.7.1 Unable to relay for outside@gmail.com'
Original message headers:
Received: from exch2019.mydomain.com (10.1.10.13) by
outside@gmail.com (outside@gmail.com)
Your message wasn't delivered due to a permission or security issue. It may have been rejected by a moderator, the address may only accept email from certain senders, or another restriction may be preventing delivery.

The following organization rejected your message: smarthost@mhydmain.com.






Diagnostic information for administrators:
Generating server: exch2019.mydomain.com
outside@gmail.com
smarthost@mhydmain.com
Remote Server returned '550 5.7.1 Unable to relay for outside@gmail.com'
Original message headers:
Received: from exch2019.mydomain.com (10.1.10.13) by
 exch2019.mydomain.com (10.1.10.13) with Microsoft SMTP Server
 (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.2.529.5;
 Fri, 10 Apr 2020 09:57:04 -0400
Received: from exch2019.mydomain.com ([::1]) by exch2019.mydomain.com
 ([::1]) with mapi id 15.02.0529.010; Fri, 10 Apr 2020 09:57:04 -0400 (10.1.10.13) with Microsoft SMTP Server
 (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.2.529.5;
 Fri, 10 Apr 2020 09:57:04 -0400
Received: from exch2019.mydomain.com ([::1]) by exch2019.mydomain.com
 ([::1]) with mapi id 15.02.0529.010; Fri, 10 Apr 2020 09:57:04 -0400

Please post the result of get-sendconnector | fl

http://mxtoolbox.com/
Please blacklist check on your IP.

[PS] C:\Windows\system32>
[PS] C:\Windows\system32>get-sendconnector | fl


AddressSpaces                : {SMTP:*;20}
AuthenticationCredential     :
CloudServicesMailEnabled     : False
Comment                      :
ConnectedDomains             : {}
ConnectionInactivityTimeOut  : 00:10:00
ConnectorType                : Default
DNSRoutingEnabled            : True
DomainSecureEnabled          : False
Enabled                      : True
ErrorPolicies                : Default
ForceHELO                    : False
Fqdn                         : gfi.mydomain.com
FrontendProxyEnabled         : False
HomeMTA                      : Microsoft MTA
HomeMtaServerId              : EXCH2019
Identity                     : direct send to outside
IgnoreSTARTTLS               : False
IsScopedConnector            : False
IsSmtpConnector              : True
MaxMessageSize               : 35 MB (36,700,160 bytes)
Name                         : direct send to outside
Port                         : 25
ProtocolLoggingLevel         : Verbose
Region                       : NotSpecified
RequireOorg                  : False
RequireTLS                   : False
SmartHostAuthMechanism       : None
SmartHosts                   : {}
SmartHostsString             :
SmtpMaxMessagesPerConnection : 20
SourceIPAddress              : 0.0.0.0
SourceRoutingGroup           : Exchange Routing Group (DWBGZMFD01QNBJR)
SourceTransportServers       : {EXCH2019}
TlsAuthLevel                 :
TlsCertificateName           :
TlsDomain                    :
UseExternalDNSServersEnabled : False

AddressSpaces                : {SMTP:*;1}
AuthenticationCredential     :
CloudServicesMailEnabled     : False
Comment                      :
ConnectedDomains             : {}
ConnectionInactivityTimeOut  : 00:10:00
ConnectorType                : Default
DNSRoutingEnabled            : False
DomainSecureEnabled          : False
Enabled                      : False
ErrorPolicies                : Default
ForceHELO                    : False
Fqdn                         :
FrontendProxyEnabled         : False
HomeMTA                      : Microsoft MTA
HomeMtaServerId              : EXCH2019
Identity                     : to GFI
IgnoreSTARTTLS               : False
IsScopedConnector            : False
IsSmtpConnector              : True
MaxMessageSize               : 35 MB (36,700,160 bytes)
Name                         : to GFI
Port                         : 25
ProtocolLoggingLevel         : None
Region                       : NotSpecified
RequireOorg                  : False
RequireTLS                   : False
SmartHostAuthMechanism       : None
SmartHosts                   : {[10.0.0.14]}
SmartHostsString             : [10.0.0.14]
SmtpMaxMessagesPerConnection : 20
SourceIPAddress              : 0.0.0.0
SourceRoutingGroup           : Exchange Routing Group (DWBGZMFD01QNBJR)
SourceTransportServers       : {EXCH2019}
TlsAuthLevel                 :
TlsCertificateName           :
TlsDomain                    :
UseExternalDNSServersEnabled : False

AddressSpaces                : {SMTP:*;1}
AuthenticationCredential     :
CloudServicesMailEnabled     : False
Comment                      :
ConnectedDomains             : {}
ConnectionInactivityTimeOut  : 00:10:00
ConnectorType                : Default
DNSRoutingEnabled            : False
DomainSecureEnabled          : False
Enabled                      : False
ErrorPolicies                : Default
ForceHELO                    : False
Fqdn                         :
FrontendProxyEnabled         : False
HomeMTA                      : Microsoft MTA
HomeMtaServerId              : EXCH2019
Identity                     : gfitest2
IgnoreSTARTTLS               : False
IsScopedConnector            : False
IsSmtpConnector              : True
MaxMessageSize               : 35 MB (36,700,160 bytes)
Name                         : gfitest2
Port                         : 25
ProtocolLoggingLevel         : None
Region                       : NotSpecified
RequireOorg                  : False
RequireTLS                   : False
SmartHostAuthMechanism       : None
SmartHosts                   : {[10.0.0.14]}
SmartHostsString             : [10.0.0.14]
SmtpMaxMessagesPerConnection : 20
SourceIPAddress              : 0.0.0.0
SourceRoutingGroup           : Exchange Routing Group (DWBGZMFD01QNBJR)
SourceTransportServers       : {EXCH2019}
TlsAuthLevel                 :
TlsCertificateName           :
TlsDomain                    :
UseExternalDNSServersEnabled : False



[PS] C:\Windows\system32>

My ip is not blacklisted

What is this IP 10.0.0.14?
You should allow IP of EXCH2019 in  10.0.0.14.  Configure IP of EXCH2019 as allowed sender IP in 10.0.0.14.

If you set your send connector to use MX record and send email to gmail you can see email is delivered. Please dont forget to check spam folder.

what is wrong with scoping * ?

again software firewall on exchange is disable
smart host is on same subnet no firewall in between
port 25 is open on the firewall to the intertnet  and I can telnet on port 25 to any outside smtp server  fine.
traffic is not reaching firewall when send directly to the internet
and email are not getting to a smarthost which is on the same subnet as excahnge severs

i connector delivery has to MX record associated
another connector to the SMART Host MS IIS SMTP connector and relaying is permitted from Exch2019
but no email received neither by smart host no by gmail .

thank you
Leo