Mac Mail Strikes Again !

A week after installing the new operating system named OS X El Capitan on my Apple MacBook Pro, I tried to send an email using my Outlook email address via the Mac Mail app. Unfortunately, I got an error message stating “The sender address was rejected by the server”. I would like to share how I fixed this issue with my fellow readers and victims.

Figure : Mac Mail running in OS X El Capitan
Figure : Mac Mail running in OS X El Capitan [1]
Follow the procedure given below :

  1. Open Mac Mail app.
  2. Click on “Mail” at the top and then click on “Preferences”
  3. Click on “Accounts” and then select the Outlook account.
  4. Under “Account Information” tab, locate “Outgoing Mail Server (SMTP)”. Click on the drop-down menu and select “Edit SMTP server list”.
  5. Make sure the information given below tallies with the ones on the pop-up window [2]

Under “Account Information” tab :

  • Server name:

Under “Advanced” tab :

  • Port: 25 (or 587 if 25 is blocked)
  • Authentication: External (TLS client Certificate)
  • User Name: *Your full email address*
  • Password: *Your Outlook password*

Finally, click on “OK” and then close the window. In the next pop-up window, click on “Save”.

Hooray ! I was able to send emails via the Mac Mail app again. Hope this helps.

Continue reading “Mac Mail Strikes Again !”

Apple Mail App, you alright mate?

Four days ago, Apple Mail app in my MacBook Pro, started to group unrelated emails from different email accounts into conversations. These had totally different recipients and subjects. Terrible, right? Well, let me go through the steps I used to solve the issue as lot of people (who are using OS X Yosemite in their Macs) are experiencing this.

Figure : Apple Mail app [1]
Figure : Apple Mail app [1]
First, I tried to rebuild the mailbox by clicking on “Mailbox” menu and then selecting “Rebuild” in Apple Mail app. The problem got solved, but temporarily. Bummer ! My next step was to contact Apple Support and they asked me to perform a manual re-indexing of the mailbox by taking the steps mentioned below :

  1. Close Apple Mail app (if it is already open)
  2. Go to the following path : ~/Library/Mail/V2/MailData/
  3. Delete every file that begins with “Envelope Index”
  4. Restart the computer and empty the Trash.
  5. Start the Mail app.

The problem was not solved. I tried re-adding the email accounts by deleting the previous ones within the Mail App. That was not the solution either. Repairing disk permissions and performing a disk repair through Disk Utility were my next moves. After realising that was not helpful, I contacted Apple Support again. Their next step was to create a new user account and see whether the problem persists. Too much work, right? Then, they asked me to reinstall OS X and if that does not help, perform a clean install. I reinstalled Yosemite by downloading it from the Mac App Store. Those grouped emails were not separated. There was no way that I was going to do a clean install as I thought that there has to be another way. Then I took the following procedure (If your emails can be accessed using a web browser, there is no need to be afraid of doing this or backing up your emails) :

  1. Close Apple Mail app (if it is already open)
  2. Open System Preferences and double-click on Internet Accounts.
  3. Remove the accounts (including Mail, Contacts, reminders…..everything !) where the emails are getting grouped unnecessarily.
  4. Open the Mail app and add the email accounts, which were removed.

Voilà! No more grouped unrelated emails!! I restarted my laptop just too see whether the problem has been solved, and it was solved indeed. However, if the problem arises again, please follow the four steps mentioned above. Also note that there is a possibility that emails in the same account (Outlook in my case) with different subjects could get grouped as well and the solution would be the same. This could be a bug in the OS X Yosemite and let’s hope that the software team at Apple will fix it soon.

Follow the above procedure if you get duplicates in the sent items as well (particularly if you have an Outlook email address). This method could also be applied if emails do not get received in your Outlook inbox within the Mail app.

References :

[1] Apple Mail app. 2015. [ONLINE] Available at: [Accessed 02 January 2015].