Hi @Jarosław Kaczmarek ,
I don't know everything about the innerworkings of this feature, but I've been experimenting with it recently and here's what I've experienced.
The portal customer user needs to "opt in" to receive notifications on an individual request basis. I assume this was built this way to give customers flexibility to choose their JSM spam. :)
I found if you add the customer to the "Shared with" area (on the right sidebar, below the transitions in your screenshot) then they receive messages even if notifications are set to "off". (This is in addition to being a member of an organization also listed in the "Shared with" area.)
I recommend telling users (either when their accounts are created, with an automation, or when requests are created) that they specifically need to "Opt in" to receive subsequent notifications. I tried to hack a way to "auto subscribe" them but didn't get anywhere on that.
I'd also try to reproduce the problem by creating a dummy customer account with a dummy email address, so you can log in to the portal and test it out.
I hope one day Atlassian also offer a profile level option, so users can choose to always be "subscribed", never be "subscribed", or leave it up to individual request settings which exists now.
I'm hoping others from the community will chime in too about their experiences with this feature.
Until then, I hope something in here helps!
Rachel Wright
Author, Jira Strategy Admin Workbook
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