On Mon, Oct 02, 2017 at 06:31:07PM +0000, Fazzina, Angelo wrote:

> smtpd[13106]: 6359630038E5: client=angelo.uits.uconn.edu[137.99.80.129]
> cleanup[13111]: 6359630038E5: 
> message-id=<39f07e3f-c6fe-642b-26b3-8964efda4...@appmail.uconn.edu>
> qmgr[13103]: 6359630038E5: from=<alf02...@appmail.uconn.edu>, size=648, 
> nrcpt=1 (queue active)
> smtp[13114]: connect to 
> uconn-mail-onmicrosoft-com.mail.protection.outlook.com[216.32.180.170]:25: 
> Connection timed out
> smtp[13114]: connect to 
> uconn-mail-onmicrosoft-com.mail.protection.outlook.com[207.46.163.106]:25: 
> Connection timed out
> smtp[13114]: 6359630038E5: to=<alf02...@uconn.mail.onmicrosoft.com>, 
> orig_to=<ang...@uconn.edu>, relay=none, delay=60, delays=0.03/0.02/60/0, 
> dsn=4.4.1, status=deferred (connect to 
> uconn-mail-onmicrosoft-com.mail.protection.outlook.com[207.46.163.106]:25: 
> Connection timed out)

Something in your configuration rewrites the recipient address from
the "orig_to" address to the "to" address. The MX host for the
nexthop domain is then:

    uconn.mail.onmicrosoft.com. MX 10 
uconn-mail-onmicrosoft-com.mail.protection.outlook.com.

with addresses (subject to dynamic load-balancing):

    uconn-mail-onmicrosoft-com.mail.protection.outlook.com.     10 IN A 
216.32.180.170
    uconn-mail-onmicrosoft-com.mail.protection.outlook.com.     10 IN A 
216.32.181.170

It seems your new server is blocked from connecting to these.
That'd be some sort of networking issue, unrelated to Postfix.

> virtual_alias_domains =
>       access.ced.uconn.edu,
>       appmail.uconn.edu,
>       eri.uconn.edu,
>       finearts.sfa.uconn.edu,
>       law.uconn.edu,
>       math.uconn.edu,
>       ropercenter.uconn.edu,
>       studentorgs.uconn.edu,
>       students.law.uconn.edu,
>       testexchange.uconn.edu,
>       uconn.edu
> virtual_alias_maps =
>       hash:/etc/postfix/virtual,
>       mysql:/etc/postfix/files/mysql_pn.cf,
>       regexp:/etc/postfix/maps/googlegroups,
>       regexp:/etc/postfix/maps/subaddressing

Given that "uconn.edu" is a virtual alias domain, the rewrite looks
normal and intended.  So tackle the networking issue.

-- 
        Viktor.

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