For a long while now, I've been tearing my hair out over a small but vexing problem: Every time I go to iCloud.com in my desktop browser, I have to jump through hoops to "verify" my identity.
That's because I've enabled two-factor authentication on my Apple account. It's a great -- some would argue an essential -- security option, but why was iCloud.com making me do it every single time? Usually, once you've approved a sign-in location (in this case the browser on my PC), you're done unless you manually sign out.
But after I signed into iCloud, I couldn't access my data without first verifying my identity, which meant sending a numeric code to an approved device (my iPhone), then manually entering that code in the desktop browser (Chrome).
I figured it had to be a browser glitch, so I cleared my cache, history and all that -- no luck. I tried another browser on the same PC -- same result. Then, suspecting some deep-rooted Windows issue, I even tried my other computer. You guessed it: "Verify your identity to access all of iCloud.com." Aaaargh!
I also searched various user forums and discovered, to my surprise, this wasn't a common issue. There were other iCloud problems, yes, but not this one. What the heck was going on?
Finally, almost by accident, I spotted the culprit. See, I use a password manager -- Dashlane -- and rely on it to automatically sign me into various websites. The next time I watched it sign me into iCloud.com, I noticed the check-box just below the username and password fields: "Keep me signed in." That box: unchecked. So Dashlane was doing its job of rapidly and automatically bypassing the sign-in screen, but also preventing me from checking that very important box.
Hence, the iCloud.com verification requirement, every single time. As far as the site was concerned, every sign-in was my first sign-in.
In Dashlane, at least, it's easy to disable automatic sign-in for any given site. Just open the entry for that site, then clear the checkbox next to Always log me into the website. Click OK to complete the setting.
After doing that, I was able to go to iCloud.com and click the Keep me signed in box before actually signing in.
Needless to say, there are some sites -- especially those with two-factor authentication, like Evernote, your bank, etc. -- that might force you into the same never-ending "verify your identity" cycle. If you're using a password manager to automatically log you in, disable it -- at least temporarily -- to make sure the site remembers you from one visit to the next.