Connect Outlook to OS X Mail
I recently received an email where a user was trying to connect his Outlook account (Hotmail) to the server on OS X Mail (Apple Mail client). He was receiving errors like
“Nov 2 18:46:14 srv-service dovecot: imap-login: Login failed: Plaintext authentication disabled: rip=18.104.22.168, lip=192.168.178.32:”
And as I tried to read insights into the problem, I found that the issue is persisting with no clear solution. It has troubled many users who are trying to do the same. Microsoft has added IMAP support to Outlook.com email, using which you can keep your emails synced with the server and a third party email client like Outlook for Windows or Apple Mail for Mac (OS X Mail).
If you are the first time user of Apple Mail and trying to connect your Outlook.com account, use the method described below. Who knows? It might work for you if you are lucky. For those, who have done it, but unsuccessfully, there is a solution in the end.
How to Connect Outlook to OS X Mail
- Go to your Apple Mail. If it is the first time, the add account will wizard will open up automatically. If it doesn’t, go to ‘File’ > ‘Add Account’.
- Now, on the wizard screen that comes next, asking for your email ID, password, and name, you can try the following.
- Enter your name, but enter any bogus or fake email address that doesn’t exist on any domain. For example – email@example.com* (note).
- Next screen will ask for your account type, Description, Incoming Mail server, User Name, and Password. Enter ‘imap-mail.outlook.com’ as ‘Incoming Mail Server’, and enter your true user ID and password of Outlook.com account.
- Next, it will ask for outgoing mail server. Here enter – smtp-mail.outlook.com, and check the box for ‘use only this server’. Also check “User Authentication”. Enter your true user ID and Password here.
- Uncheck the box “take account online”. You do not want to sync to the server yet. Click “Create”.
- Select your account from the left window pane, and all your information will apear. Double check them and to see if everything is correct. You will still see the bogus email address that you entered in first step. Now, it is time to change it to the correct. Enter “yourTrueId@outlook.com” here. And click “Save”.
The account will be by synced to the Outlook servers in no time and you can see all your folders here.
*Note – The point of entering the wrong email ID is to bypass Apple Mail’s automatic attempt to switch the account to POP. As soon as Apple Mail sees ‘Outlook.com’ account, it will switch it to POP and by entering a fake email ID, we trick Mail to not do that.
All is set and ready to go!
What if it still doesn’t work
There are many reports saying that Apple Mail still doesn’t create the account or sync properly with the server. This is seen again and again in many Mac computers, and there is no direct solution either by Apple or by Microsoft to solve it. And we have to wait for it.
Till then, there is a solution for those who have Windows PC and use Outlook desktop client to manage their emails. Clearly, Outlook client shouldn’t have any issue adding and syncing your Outlook or Hotmail.com account. If you haven’t done it yet, you can do that simply by going to “add account” and entering your credentials for outlook.com account. It doesn’t even ask for incoming and outgoing mail server. Everything is done automatically for you. In some cases, Outlook may ask to install a small program that make things more streamlined.
Once it is set-up, you can export the data to the Pst file. Pst file is the primary file format for Outlook to store all the contents in archived format.
What to do with the Pst file?
With Pst file, you can’t simply import it into Mac OS X Mail. You have to convert this Pst file into Mbox format for Apple Mail.
To do that, download a very effective tool called “Pst Extractor Pro” here. This is the link for its free limited edition. If you want to convert without any restriction, you have to purchase the full license.
The tool is very easy to work with. All you have to do is simply load up your Pst file that you created a while ago using Outlook email client. Once it is loaded up, the tool will display the folders inside it, and you can select the folders you want to convert. Select all if you don’t want to exclude any data. Finally, choose the output format as “Apple mail, Address book, Calendar (iCal)” and click “Convert.
PST Extractor Pro for Converting Data
The tool will then start the conversion process and extract all the data from the Pst and implement into newly created Mbox file. There are few additional options as well that you can tweak. Such as splitting Mbox file if it exceeds the limit (limit can be manually set), saving read/unread emails in separate folders, and merging contacts and calendar data into Vcf and Ics file respectively.
Once the tool has completed the conversion, you can import the Mbox file into Apple Mail without any issue. This, however, doesn’t add your actual online account of Outlook to OS X Mail, and thus you can’t sync.
However, this is one of the best and easiest way to bring over all your data from Windows Outlook client to Mac Mail. Also, it doesn’t corrupt any email data, and the conversion is always pretty accurate and thorough. It will preserver everything from attachments to images to email properties and even to all non-English text.
Download the free copy of “Pst Extractor Pro” here (https://www.uslsoftware.com/download/pst-extractor-pro/).