Written by Jennifer Walsh. Reviewed for technical accuracy by Shubham Dixit, Independent Expert in Email Forensics and Data File Conversion. Updated 18 September 2026.
Shubham is an independent external reviewer and not an employee of PCDOTS.
Quick answer. MSG is Outlook’s email file, and iCloud Mail is an IMAP account. There’s no direct import button, so you add iCloud in classic Outlook with an app-specific password, then drag the MSG emails into the iCloud folder and Outlook uploads them. A tool does the same in bulk without Outlook. The same steps move a PST or any Outlook mail into iCloud.
On this page
- What does importing MSG files to iCloud involve?
- What iCloud settings and password do you need?
- How do you import MSG files to iCloud with Outlook for free?
- Why won’t iCloud connect in Outlook?
- How do you import MSG files to iCloud in bulk without Outlook?
- Which method should you use?
- Frequently asked questions
What does importing MSG files to iCloud involve?
MSG is Outlook’s format for a single email, held on your computer. iCloud Mail is an IMAP account that keeps mail on Apple’s server and syncs to every Apple device. The same settings cover @icloud.com, @me.com and @mac.com addresses.
People import MSG files to iCloud to read old Outlook mail on an iPhone or Mac, to keep a server copy that survives a dead PC or to leave Outlook behind for the Apple ecosystem.
There’s no button that drops a MSG file straight into iCloud. So importing MSG files to iCloud means connecting iCloud inside Outlook, then moving the emails into the iCloud folder, where Outlook uploads them to the server.
The same route works for more than MSG. A PST file or any mail already in Outlook imports into iCloud the same way, by dragging it into the iCloud folder.
Outlook uploads the MSG mail to iCloud, which syncs to every Apple device.
“iCloud Mail is just an IMAP account, so once it’s in Outlook you drag the MSG emails into it and they upload. The one thing that trips almost everyone is the password. Apple makes two-factor mandatory, so Outlook will not accept your normal iCloud password, you generate an app-specific password at appleid.apple.com and use that instead. Get that right and the settings are simple, imap.mail.me.com on 993 with SSL. The same drag works for an entire PST, and for a big mailbox a tool that uploads straight to iCloud without Outlook saves the waiting.” Shubham Dixit, Email Migration reviewer (draft, pending approval)
What iCloud settings and password do you need?
You need the iCloud IMAP settings and an app-specific password. This password is the step people miss, and it’s why the connection fails with a wrong-password error.
Apple makes two-factor authentication mandatory on your Apple ID, so Outlook won’t take your normal iCloud password. Go to appleid.apple.com, open Sign-In and Security, select App-Specific Passwords, generate one and label it Outlook. Use that password in Outlook. If you run Outlook 2021 or later, you can sign in with your Apple Account instead.
iCloud Mail settings for Outlook
- Incoming server, IMAP. imap.mail.me.com, port 993, SSL.
- Outgoing server, SMTP. smtp.mail.me.com, port 587, STARTTLS.
- Username. Your full iCloud email address.
- Password. An app-specific password from appleid.apple.com, not your normal one.
Two quick checks before you start. Turn iCloud Mail on in your iCloud settings, since IMAP rejects the connection if Mail is off. And watch your storage, a free iCloud account holds 5 GB shared across Mail, photos and backups, so a large mailbox needs an iCloud+ plan for the extra room.
How do you import MSG files to iCloud with Outlook for free?
You import MSG files to iCloud for free in classic Outlook. Connect iCloud as an IMAP account, open the MSG files, then drag them into the iCloud folder. Outlook uploads them.
Here are the five steps.
- Generate an app-specific password at appleid.apple.com, so Outlook can sign in to iCloud.
- In classic Outlook, add iCloud as an IMAP account, File then Add Account, with the settings above and that password.
- Open your MSG files in Outlook, by double-clicking them or dragging them into a folder.
- Select the emails and drag them into the iCloud folder in the Outlook sidebar.
- Wait while Outlook uploads them, then check iCloud.com or your iPhone to confirm.
The first time I set this up, I used my normal Apple password and it kept failing. The fix was the app-specific password, and after that the upload ran on its own.
Connect iCloud, open the MSG mail, drag it into the iCloud folder.
Why won’t iCloud connect in Outlook?
If iCloud won’t connect, the cause is almost always the password or a setting. Here are the fixes that clear most errors.
- Wrong password error. You used your normal iCloud password. Enter the app-specific password from appleid.apple.com instead.
- Cannot connect to server. Check the ports, 993 with SSL for IMAP and 587 with STARTTLS for SMTP. One wrong number stops the sync.
- Nothing syncs. Confirm iCloud Mail is turned on in your iCloud settings, or the server rejects the connection.
- Sending fails but receiving works. In More Settings, Outgoing Server, tick that your SMTP server requires authentication.
- Still blocked. A firewall or antivirus can block port 587, so test with it paused. If the app password stopped working, revoke and regenerate it.
Most iCloud connection errors trace back to the password or a port.
How do you import MSG files to iCloud in bulk without Outlook?
You import MSG files to iCloud in bulk without Outlook by using a converter that uploads straight to the account. It reads the .msg files and transfers them to iCloud over IMAP, so there’s no dragging and no waiting on Outlook.
PCDOTS MSG Converter loads a folder of MSG files and exports them to iCloud in a single operation. It uses the server, port, email and app-specific password to upload, and keeps the folder structure and attachments. It runs on Windows without Outlook. The free trial moves the first 10 files, so you can test the connection first. Follow these four steps.
- Install and run PCDOTS MSG Converter, then open the menu.
- Add your MSG files or an entire folder.
- Open Export and select IMAP.
- Enter your iCloud email, app-specific password and server, then start the upload.
The tool route, a folder of MSG files uploaded to iCloud at once.
Here are the same four steps with the screens.
Step 1. Install and run PCDOTS MSG Converter.
Step 2. Add your MSG files or an entire folder.
Step 3. Open Export and select IMAP.
Step 4. Enter your iCloud email and app-specific password, then start.
Related reading, our guides to import MSG to Yahoo Mail and convert MSG files to CSV. To check a file first, the free MSG viewer opens a .msg without Outlook.
Which method should you use?
Use Outlook’s drag for a few MSG files, and a converter for a big batch or when Outlook isn’t set up.
| Method | Best for | Good to know |
|---|---|---|
| Outlook drag to iCloud | A few MSG files | Free, needs classic Outlook |
| MSG Converter | A big batch, no Outlook | Windows, uploads over IMAP |
Key takeaways
- iCloud Mail is an IMAP account, so you import MSG files through Outlook, not a direct button.
- You must use an app-specific password from appleid.apple.com, not your normal iCloud password.
- The settings are imap.mail.me.com on port 993 with SSL, and smtp.mail.me.com on port 587.
- A converter uploads a batch of MSG files to iCloud over IMAP without Outlook.
Frequently asked questions
Can I import MSG files to iCloud without Outlook?
Yes. A converter reads the .msg files and uploads them to iCloud over IMAP, so Outlook does not need to be installed.
Why won’t Outlook accept my iCloud password?
Because Apple requires two-factor authentication. Generate an app-specific password at appleid.apple.com and use that in Outlook, not your normal iCloud password.
What are the iCloud IMAP settings?
Incoming is imap.mail.me.com on port 993 with SSL. Outgoing is smtp.mail.me.com on port 587 with STARTTLS. iCloud does not support POP3.
Can I import a PST to iCloud the same way?
Yes. Open the PST in Outlook and drag its folders into the iCloud account. The upload works the same as it does for MSG files.
Do my attachments and folders stay intact?
Yes. Dragging into the iCloud account and a good converter both keep attachments and the folder structure during the upload.
Where do the emails appear after importing?
In your iCloud Mail, so they show up at iCloud.com and on the Mail app on your iPhone, iPad and Mac once they sync.
Ready to move your mail to iCloud?
Importing MSG files to iCloud comes down to two things, an app-specific password and the IMAP settings. With those in place, classic Outlook lets you drag the emails into the iCloud folder for free, and a converter uploads a big batch without Outlook at all. Either way the mail lands in iCloud and syncs to your iPhone, iPad and Mac. So which fits you, a quick drag of a few files, or a batch upload of the lot?
