in windows server how to check connectivity to remote server with required ports is open or not

Dear Experts

We have hosted CRM application  on-premises which is web-based and every user has email settings to be configured, the email server is on internet and also other integration like SMS(sms service provider is on external network) and third party applications, all these were perfectly working until the recent changes at the gateway level and internal IT policy,  I suggested them may be the crm servers are not allowed to talk to the external network of email server and sms service providers,.
please find the attached error logs captured, and these the crm server is of windows server 2012R2 can you please help on how to test and confirm to them based on test result like the issue of connectivity, is it recommend to telnet from the web-application crm windows server to the destination email server/sms sever provider server with the ports -- is this the right way OR any other way to check and ensure the necessary ports and access at the gate way/firewall is opened or not, please suggest.
issues.txt
D_wathiAsked:
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masnrockCommented:
It looks like you are asking about outbound connections. If that is the case, then telnet is a good approach. Traceroute might help, especially if you can get to a hop outside of the router. Another thing that comes to mind is finding out if any changes were made at O365.
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matrix8086Commented:
It looks like the settings have been reset, or never been configured: SMTP Mail server: mydomain-com.mail.protection.outlook.com. I don't think that you domain is mydomain-com.

The same problem on SMS: api.mydoamin.com. MYDOAMIN.COM is realy your URL where you want to connect to?

Maybe the same thing on IMAP ...

Good Luck
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D_wathiAuthor Commented:
thank you very much for the reply.  mydomain.com is replaced form the original it was done by me intentionally. can I try with -portqry application.  as mentioned trace route will be helpful. it is office365 accounts and will have to find actual smtp server and port. please let me know will portqry will be helpful
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masnrockCommented:
That won't help because the problem is the CRM system is initiating a connection to the mail server. Portqry only helps in cases where you're expected inbound connections.

Did you try port 993 for IMAP? Also make sure that you have it set for SSL. For SMTP, try port 587 (using TLS). You should always be using the secure protocols whenever possible.
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matrix8086Commented:
OK. I never used portqry, but according to its ddescription it can be useful. As far as I know, Office365 accepts only secured connections, and your ports are not for secured connections. IMAP over SSL is 993 and SMTP over SSL is 587.

Best regards
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masnrockCommented:
As for your third connection issue, check with the IT team. Also, are https connections available for that site? If so, try that and see if it works.
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D_wathiAuthor Commented:
they for inbound they are using outlook.office365.com
imap and port 143
and for outbound internal smtp mail server on port 25.
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D_wathiAuthor Commented:
as the issue of outbound mail not getting delivered from CRM system,  as a first step is it important to test the server level that is through tracert and telnet for smtp connection establishment if it does not work here then it will not work in crm system please suggest is this correct.
2. similarly for incoming email server also tracert and telnet
please suggest.
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masnrockCommented:
they for inbound they are using outlook.office365.com
imap and port 143
and for outbound internal smtp mail server on port 25.
You do know these are the ports used for insecure communications...

Try what I suggested, which should have the CRM communicating over secure ports.

Also, I would recommend what changes exactly were made. Without that information, it becomes harder to guess what the cause of your issues might truly be.
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D_wathiAuthor Commented:
thanks for the reply, have asked the system admin/IT  to perform the tracert and telnet testing on the CRM system. for incoming imap and out going smtp. this as first step, hope this is the first step and then look at the crm application side.
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Jeff GloverSr. Systems AdministratorCommented:
First thing. On your CRM server, you should use Telnet client to check if port 25 responds. Also, are you allowing the CRM server IP to relay via Exchange? That needs to be done also before Exchange will respond. Although you use IMAP, your error specifies SMTP as failing so make sure you have a receive connector that allows anonymous auth and has the IP of the CRM server as an allowed relay.
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D_wathiAuthor Commented:
Hi Jeff Glover
Thanks for the reply, yes in the crm email settings for incoming hostname is configured as outlook.office365.com and port 143 and SMTP outbound server is internal server (on -premises)  and on port 25
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Jeff GloverSr. Systems AdministratorCommented:
Ok. Glad you found the solution.
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