Hotmail to iCloud transfer problem.

Question

Hotmail to iCloud transfer problem.

Good morning everyone. I’ve used Hotmail since 1997. In 2008 I added a second email address and happily used both (one personal, one work) on Apple Mail until the autumn when Microsoft emailed to say that Apple wouldn’t support this anymore. I then used the Outlook app but on my MacBook it had limitations such as not appearing on the options when trying to share a document and on the iPhone the Apple Mail option kept popping up when I pressed email links in websites; all rather irritating.

As yesterday was wet I decided to try to move my email addresses to new @icloud.com ones thinking all Apple products would smooth operation. I called support for help and screen shared with them to do this. I had to set up forwarding on both my old Hotmail addresses in outlook.com and then laboriously create the same folders and sub folders in Apple Mail as in my outlook and move all the emails across.

Unfortunately there are problems.

1. I’m only receiving emails from Apple and nobody else even though forwarding is definitely on in outlook.

2. The work email address isn’t a separate entity. It’s just one folder in the general email folders.

3. Email signatures have to be chosen every time I write an email (not that I’m writing any - see point 1.).

Can anyone help please? I just want a simple set up with my two (new) iCloud.com email addresses receiving emails. I also need anyone who has saved one of my @hotmail.com addresses to know they've changed to iCloud.com

Here’s a couple of screenshots

The highlighted folder is/was my work email address inbox but in outlook (and in Apple Mail before September) it looked like a separate account with its own inbox/sent items/deleted items etc.

Hoping someone can help with this,

James

MacBook Air (M3, 2024)

Posted on Dec 18, 2025 12:50 AM

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Answer 1

zinacef

Level 10

88,786 points

Dec 18, 2025 6:13 PM in response to Appleydappley

It sounds like you have transitioned from a multi-account setup to a single-account setup with nested folders, which is causing the organization and signature issues you're seeing. When you create a single iCloud account and manually move Hotmail folders into it, Apple Mail treats those folders as standard storage directories rather than independent "Accounts" with their own specific settings.

To resolve the separation of your work and personal emails, you should ideally have two distinct iCloud aliases or accounts. In your current view, the "Work" folder is simply a sub-folder of your primary iCloud Inbox, which is why it doesn't have its own Sent or Bin sections. To get that "separate account" feel back, you would need to go to Settings > Mail > Accounts and ensure both addresses are recognized as distinct entities. If you are using one iCloud account for both, you can manage aliases at iCloud.com, but they will often still share a single Sent and Trash folder within the Apple Mail interface.

Regarding the forwarding issue, if you are only receiving emails from Apple, there may be a "Syncing Paused" status or a verification requirement within your Hotmail/Outlook settings. Sometimes, Microsoft requires you to "Verify" the forwarding address via a confirmation email before it begins sending third-party traffic. If the status in your Mail app shows "Updated Just Now" but the messages aren't there, double-check the Junk folder in both Outlook.com and Apple Mail, as forwarding can sometimes trigger spam filters.

For your signatures and notifying your contacts, you can automate the transition to save yourself the manual labor. In Apple Mail on your Mac, you can go to Settings > Signatures and assign a specific signature to each "Choose Account" on the left so it defaults correctly when you compose a message. To notify your contacts, the most effective method is to set up an "Auto-Reply" on your old Hotmail accounts. This way, anyone who emails your old address receives an instant message stating: "My email has changed to [your name]@icloud.com. Please update your address book."

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