Earlier quoted context omitted.
Rule #1 if you're applying for jobs or graduate school - Don't use gmail for your email address. Source: Led a hiring committee this year. Interview invitations and job offers went straight to the junk mail folder. Also serve as Director of Graduate Studies. Admissions and funding offers, as well as general inquiries about availability, all went straight to the junk mail folder. We're not going to change our email se…
Indeed, the spur for me to finally sign up for Fastmail was that I was applying for a job and I can't trust Google with crucial email. You get what you pay for.
There's a high 9's probability that it will arrive safely, but there's several ways that things can go wrong, simplest of which is that you are deleted by a misconfigured filter.
There are US ISPs (cough sbcglobal) that routinely throw away mail from some arbitrary IPs despite there being absolutely no SPAM blacklist entries for the IP, even if you are replying to a mail sent from one of their clients.
outlook.com once, (and maybe still does) blocked email from an entire C-block for some reason.
(edit - grammar)