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I'm not sure I see the XSS vuln, or rather, a site might have an XSS vuln and long sessions would make it worse, but I don't see long sessions causing XSS. MitM would be possible without TLS, but not with it. Malware is always a threat, but if it can read cookies it might be able to read cached passwords etc. too.

Sure you don't want to constantly bug the user but not every site needs to do that. Especially for sporadically-used sites, "receiving email" could be less of a pain than keeping track of passwords.

A session can be long-lived without being indefinite. We might decide that any authenticated site visit within the last week is new enough not to repeat the passwordless process, or we might say two weeks or a month or whatever.




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