I'm trying to send an email to an address that I've sent to several times before, but Gmail does not autocomplete it. Is this expected behaviour? Must I add that address as a contact before Gmail can search it?
Gmail – Why Email Addresses Are Not Found
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Best Answer
It would seem so.
You've probably turned off this setting, in order to keep Gmail from adding just anybody to your contacts.
According to Gmail Support
So, in order for the auto-complete to work, the person/email address needs to be in your contacts. Your browser may have offered auto-complete before (if you set it to do that with web forms) but Gmail's fields are far from being simple HTML input fields.
If the person is in your contacts and still not coming up in auto-complete, then Google suggests that it's probably your browser. Use a different one or, if you're sure it's supported, clear your browser cache.