Thanks Dusan and Wietse, I searched in postfix log files and I can
confirm that looping emails have the same ID. "Normal" emails ID
appear in the log files a few times (depending on the number of
recipients I suppose), but looping emails appear many times:

14 times 
db8p195mb0565dd65da92d1861c8946u48c...@db8p195mb0565.eurp222.prod.outlook.com
14 times 
vi1p195mb02560627a8aa5227c95208cd80...@vi1p195mb0256.eurp222.prod.outlook.com
14 times 
vi1p195mb0463506au7u3dc47au795a8u92...@vi1p195mb0463.eurp222.prod.outlook.com
16 times 
vi1p195mb038452d8411bu9ba5078801au6...@vi1p195mb0384.eurp222.prod.outlook.com
17 times 
db8p195mb0696625u1739d7u4dcaa889991...@db8p195mb0696.eurp222.prod.outlook.com
18 times 
db6p195mb02635592256ud2d84241d3a882...@db6p195mb0263.eurp222.prod.outlook.com
20 times 
pr3p195mb06990241a503dc8b8656d5u9aa...@pr3p195mb0699.eurp222.prod.outlook.com
20 times 
vi1p195mb0463aau9au1a022a1cuu68a692...@vi1p195mb0463.eurp222.prod.outlook.com
22 times 
pr3p195mb07470b722a0a5a241d51dad684...@pr3p195mb0747.eurp222.prod.outlook.com
32 times 
vi1p195mb03187a8b7275d41b023cc2a0a5...@vi1p195mb0318.eurp222.prod.outlook.com
34 times 
vi1p195mb03181c1955d18u1d423860caa5...@vi1p195mb0318.eurp222.prod.outlook.com

I think I'll try with Dusan advice and let you know. Feel free to
suggest something else if comes to your mind.


Il giorno mer 18 mar 2020 alle ore 16:40 Wietse Venema
<wie...@porcupine.org> ha scritto:
>
> Dusan Obradovic:
> >
> > > On Mar 18, 2020, at 11:45 AM, ego...@gmail.com wrote:
> > >
> > > host xxx-xxx.mail.protection.outlook.com[X.X.X.X] said: 554 5.4.14 Hop
> > > count exceeded - possible mail loop ATTR1
> > > [xxx-xxx.prod.protection.outlook.com] (in reply to end of DATA
> > > command)
> > >
> >
> > I suspect this is based on received headers.
> >
> > > Is there a way in Postfix to
> > > "mask" (?) source IP and avoid this loop? Do you have better ideas?
> >
> > Alternatively, You could remove some of the existing Received: headers with 
> > Postfix.
> > See http://www.postfix.org/header_checks.5.html
>
> That is a dangerous solution as it could cause mail to loop forever.
>
> To find out if there actually is a hopcount problem, look for the
> message ID of a looping message.
>
> Exmnple:
>
> Mar 18 00:56:32 spike postfix/cleanup[71391]: 48hyS02vZDzJrNs: 
> message-id=<48hys02vzdzj...@spike.porcupine.org>
>
> The message ID is "48hys02vzdzj...@spike.porcupine.org".
>
> If mail is really looping then you should see that message ID
> going through your mail system repeatedly.
>
> If mail is not really looping, then Microsoft may be reporting
> a hopcount error for other reasons, and using a different
> source IP address may help.
>
>         Wietse

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