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Why I Hate Software (I Don't Really But Microsoft And Apple Are Still Frenemies)

Setting up iCloud on one Windows laptop actually went smoothly. Every tool did exactly what it was supposed to do. This, even though I have combined my vanity email domain with iCloud.

To be fair, I actually send email from my personal account only slightly more often than I phone people from my personal number, which is close to (but not quite) never.

On a desktop, this did not happen. Even with Office365 installed, the iCloud tool only synced calendars and contacts. The Apple installer told me if I need iCloud email, to set up an address online.

I also could not use my primary email address, which matches my AppleID, to set up my mailbox in Outlook. I had to use the original email address, and set up an application password through my AppleID, in order to set up the service.

Possibly related, in the past I have used Google to host my vanity domain. Whenever the Outlook email setup wizard walked me through account setup, it wanted me to authenticate to Google. I don’t know if that is residual in Microsoft365, or if there is something in DNS that is making Microsoft go there. I really thought I had cleaned house at my provider.

In the end, I can monitor my mailbox from a second Windows PC. That is what I needed. But the process took the better part of 2 hours of experimentation, including waiting several times on a “We’re getting things ready” message from Outlook while nothing happenned in the GUI.

None of the Apple machines ever have trouble, and I was aware that doing iCloud on Windows could present challenges. But when things actually behaved well on one Windows 11 machine, I had hope it might go equally well on another.

All of this to avoid the security hoops signing into iCloud through a web browser, or simply checking email on my phone. I want to avoid transcribing password reset links or login links. Even NVidia nags for a login for video drivers, holding some software functions hostage to it.

As in all things technological, some days it’s deeply challenging to make software do the thing it is meant to do. I blame both companies for making me use wizards, and not giving me the option to set things manually. Even with the mailbox established, I cannot dig into Outlook to see what settings the software is using to connect (server names, ports, security protocols)

So, if you can’t set up your iCloud mailbox in Outlook via the iCloud application, use the original email address ( didn’t work for me) to set up an IMAP account. Use an application password that you will generate at for the password. Nothing I found online says it exactly that way, especially for those of us who have the vanity email domain.

Lastly? You will be sending as your iCloud address, or via your default account in Outlook. I can theoretically use a reply-to address, but I think that looks sketchy.