Apple Mail – Unable to send or receive

Send & Receive issues are the most complex to troubleshoot. There are many variables that need to be checked. Usually when messages are not sending or receiving, it’s a result of Mail not remembering your password. You can check in Connection Doctor. Under Window in the Menu bar, select Connection Doctor.

connection doctor

You will see green to indicate a connection and red to show there is a problem. You want to see all green symbols.

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Before upgrading to El Capitan Mail

Before upgrading to El Capitan, you first want to clone your drive. While a Time Machine backup is a good option, if you need to revert to your previous OS X a clone is much easier and quicker than Time Machine. I suggest SuperDuper to clone your drive. SuperDuper is free to do an erase and clone. You can purchase to do schedule and smart backups. If you don’t have an external drive, check out this 3T Western Digital drive. (the 2T is often only a few dollars less). You can partition the drive and use it for clone and Time Machine.

If you are running Snow Leopard 10.6, Lion 10.7, Mountain Lion 10.8, I would suggest doing a clean install of El Capitan 10.11. If your version of OS X is 10.9 or higher, you can try upgrading El Capitan over your current install. You can always revert to the clone. Erase the internal drive and reinstall El Capitan if you find a clean install is warranted. (be sure to save the El Capitan installer. It can be found in Applications. It’s named “Install OS X El Capitan”. By default Apple deletes the installer after the install is finished.)

I’m going to focus on Apple Mail in this article. See 6 Steps to Prepare a Mac for the OS X El Capitan Update for other helpful tips before you upgrade.

Mail in 10.11 is imported from V2 to V3 folder.  See Clean up Mail folder to free up space from your drive and  Troubleshooting Apple Mail in OS X 10.11 El Capitan for more info. This import process has been troublesome for many users. I suggest you do a clean install of Mail to avoid any upgrade issues.

Before you upgrade to OS X 10.11 El Capitan.

In Mail, remove all your IMAP accounts and any Exchange accounts. Removing the account in Mail > Preferences will take you to System Preferences > Internet Accounts to remove. Simply uncheck Mail. When you add back in El Capitan all your settings will be remembered. You might need to add password again so be sure you have your passwords handy.

When you remove a POP account, the Inbox messages are removed from Mail. Be sure you export your data before removing a POP account. If the messages are no longer on the server or you do not have a backup of your Mail folder, you would loose the Inbox messages.

You can use Apple’s export as Apple Mailboxes or you can export with this third party option, Emailchemy.  If you have lots of subfolders you’ll find that Emailchemy is worth every penny.

Export a folder in Mail

Under Mailbox in the Menu bar select Export Mailbox. You will need to do this for every folder and subfolder.
Mail-Export

Use Emailchemy to export your folders.

Download Emailchemy.  The demo will mask subject and sender fields in the converted email. Please try the demo before purchasing. This will save all the folders in Mail. Your folder sturcture will be saved. To purchase: $29.95

  • Select Apple Mail to convert

EC-Import

  • Select your Mail folder. By default Emailchemy will show the correct path.
  • Select Convert

EC-Import2

  • Select your destination folder. Desktop is selected in this image.
  • Save as MBOX file (standard mbox). This saves all your folders and subfolders. You keep your folder structure.
  • You can delete the converted_email folder after importing or save to an external drive then delete.

EC-Import3png

After you have saved all your local mailboxes, in your User’s Library….

  1. Scroll down to Containers folder > delete the com.apple.mail folder
  2. Delete the Mail folder. Iif you do not have a Time Machine or clone backup of Mail simply rename to Mailxx. After you are satisfied with your El Capitan Mail upgrade, you can delete the Mailxx folder in your User’s Library.
  3. Restart and delete the Trash

Now you are ready to upgrade to El Capitan.

After the OS X 10.11 El Capitan install,  go to System Preferences > Internet Accounts to add back your accounts. I suggest you add one account at a time. Let the account download fully before adding your other accounts. Some IMAP accounts need to have the Drafts, Trash and Junk folder set correctly.

usethismailbox

Import the local “On My Mac” folders.

Under File  select  Import Malboxes…

Mail-Import

If you used Mail to export, select Apple Mail.

If you used Emailchemy select the bottom option: Files in mbox format

Mail-Import.

Using either option you will find your folders under Import folder. Toggle open to view. You can move out of Import folder by dragging to the “On My Mac” header.

import-folder.

You can select to move the messages in default folders (Inbox, Drafts, Trash, Junk) under Import back to the top folders for your POP accounts. Note if you left messages in the Inbox on the server, you will have duplicates. Before adding the imported Inbox messages back, delete any newly download Inbox messages that are in your Imported Inbox

If you need personal assistance, you can contact me for support.

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Clean up Mail folder to free up space from your drive

Free up space from your drive after upgrading OS X.

Unless you have done a clean install of OS X, you might want to check your Mail folder to delete any old files that are no longer being used.

Apple Mail stores your data in your User’s Library. Unhide your User’s Library folder and locate Mail folder to get started. Continue reading

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Troubleshooting Apple Mail in OS X 10.11 El Capitan

The Apple Mail upgrade process in OS X 10.11 El Capitan has been problematic for many users. Let’s look at what has changed and optons to fix a bad upgrade.

Apple Mail is stored in your User’s Library. Apple hides User’s Library by default. You’ll need to unhide in order to continue. How to enable the User’s Library folder

Since OS X 10.7 (Lion), Mail has been stored in the User’s Library > Mail > V2 folder. Starting in OS X 10.11 El Capitan, Mail is stored in User’s Library > Mail > V3 folder.

This screen shot shows my V2 folder compared to V3 folder.

Compare V2 folder to V3

This is an example of a V3 folder with a bad upgrade. As you can see, it’s a mix of old folders with new.

upgradev3

To Repair Mail in El Capitan follow these steps.

Step 1: Make sure you have backup. If you have Time Machine or clone backup you are covered. If not, be sure to duplicate your Mail folder in the User’s Library.

Step 2: Quit Mail

  • In System Preferences > Internet Accounts, uncheck Mail for each account.
  • Go to the User’s Library
    • Scroll to Containers. Drag the com.apple.mail folder to the trash.
    • Scroll to Mail. Drag Mail folder to the trash.
    • Scroll to Preferences. Drag any com.apple.mail.plist files to the trash
  • Log out under the Apple in the Menu bar
  • Log in
  • Empty the Trash. If not, Mail will continue to try and use data in the Mail folder.
  • Open System Preferences > Internet Accounts and check Mail for your primary account. I suggest adding one email account at a time.
  • Open Mail and test account.
  • For IMAP and Exchange users with no local messages under “On My Mac” there is no step 3 required.

Step 3: Import messages stored under “On My Mac”

Option 1) Use a Time Machine backup. Go back in time just prior to OS X 10.11 El Capitan upgrade. You should only see a V2 folder in Mail.

  • If you are in your User’s Library > Mail folder, enter Time Machine.  Restore the V2 folder to the Desktop. Follow step 2 to import the data into Mail.

Or

  • If you are in Mail under “On My Mac” folders (you’ll need to create a folder if one does not exist to see “On My Mac”) you can enter Time Machine in this view then go back in time and select to restore your folders.

restore from tm

Option 2)  Under File in the Menu bar select Import Mailboxes…

File-import

Select Apple Mail

File-import.

Navigate to your Mail backup folder. Select Mailboxes folder in V2 > Import.

(Most users did not export mailboxes prior to upgrading but if you did, navigate to your exported folders)

Your messages will show up under “On My Mac” in a folder named Import. It will most likely be at the bottom of your folder list and not listed alphabetically.

File-import..

Occassionally, I have seen importing from V2 to show messages formatted incorrectly. If you cannot export from Mail in a prior version of OS X, you can use Emailchemy to convert these to mbox files that will import in the correct format. Emailchemy has a demo you can try first. $29.95 to purchase.

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No Mail Sounds with POP Accounts El Capitan v10.11.1

Apple issued a fix for no mail sounds in OS X 10.11.1. However the fix is only working for users with IMAP accounts.

I verified this by creating a new User as a blank canvas for testing.

  • I added a new POP account and tested. No sound.
  • I deleted the POP account and added it back as IMAP. Now I get sound when receiving.

Is this a bug or by design? It’s hard to understand how sound can work for IMAP and Exchange but not POP if not by design. Users need to send Apple Feedback so it can be logged and put in the queue to be fixed. http://www.apple.com/feedback/macosx.html

In the mean time, the only workaround seems to be to create a rule to play a sound. See this example by ThoughtForce on Apple Discussions.

I suggest all users with POP accounts switch to IMAP if possible. Most email providers offer IMAP as an option now.

What’s the difference between IMAP and POP?

IMAP works by keeping mail on the server. All folders (Inbox, Drafts, Sent, Trash) including your custom folders are saved on the server.

POP works by downloading from your Inbox only. If you read on one device, the read status will not be reflected on other devices. If you delete from server the message only exists on your Mac.

Moving to a new computer or recovering from a crash, IMAP is the easiest option with no loss of data.

By default, Mail will setup most accounts as IMAP. However if you have your account set as POP you will need to remove the account first then add it back as IMAP.

Before deleting your POP account in Mail, any messages in your POP Inbox will need to be saved. Create a mailbox (folder) under “On My Mac”. Move all the Inbox messages for the POP account to this folder. Do this for every POP account that you have. When you remove the POP account, Mail deletes all messages in the Inbox. It does not delete messages in your other folders.

If your provider is not in Apple’s default setup, check your email provider for setup instructions. If your provider does not offer IMAP there are many good free options you can use [ iCloud, Comcast, Yahoo, Gmail, AOL, MSFT’s (Hotmail, Live, MSN, Outlook.com)]

If you need assistance switching to IMAP, you can post a comment for help.

 

 

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Set up Gmail POP account in Apple Mail

By default, Apple will setup your Gmail account as IMAP when you enter your Gmail address and password. However, if you prefer Gmail as POP, you have to manually setup the account. If you already have the account started as IMAP you must delete this account and create a new account as POP. You cannot change the settings on an IMAP account and make it POP.

Set Gmail as POP in your browser settings. Log in to Gmail account. Under the gear, select Settings > Forwarding and POP/IMAP. Select Enable POP. If you do not want your All Mail folder to download, select the second option “Enable POP for mail that arrices from now on”

settings

These directions are for Mavericks Mail. 

Select Add Other Mail Account… not Google.

add_account_type

Continue

add_account_type.

Enter your Email address and password > Create

add_account_type..

  • It will default to IMAP. Select POP
  • Change imap.gmail.com to pop.gmail.com
  • Enter full email address. Password should automatically be entered.

add_account_type...

Use SSL Port 993 : Authentication > Password

add_account_type....

Set outgoing server (SMTP) Enter full email address and password. Create

add_account_type.....

Enter Port 465, check SSL, Authentication > Password

Verify Settings:

Incoming:  Verify your results in the main account window for outgoing settings. If you make any changes in this window under any of the tabs, you need to click out of the window and select SAVE before the changes are saved.

add_account_type......

Outgoing:  Outgoing Mail Server SMTP:  select Edit SMTP Server list… SMTP settings..

Select account in the list. (It’s not uncommon to find extra SMTP servers listed. When you remove account, Mail does not delete the smtp info. You might need to do some clean up in the list to remove any extras.)

add_account_type.......

  • Enter name for account Gmail POP under Account information.
  • Click on Advanced tab. Verify your settings.

Use Connection Doctor to test connection

Under Windows in the Menu bar select Connection doctor.

connectiondoctor

You will see green to indicate a connection and red to show there is a problem. You can click on Show Detail button, but with multiple accounts this is often hard for some users to read results. Except for iCloud account you’ll see two entries for each account 1) receiving and 2) SMTP for sending.

If SMTP is red, recheck password was saved in the Edit SMTP settings under the advanced tab.

As you can see the fake POP Gmail I setup with Yourname@gmail.com is not connecting, but my Gmail IMAP is connected.

connected

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Use Gmail with Mavericks Mail

Like many users, I have had problems using my Gmail account with Mavericks Mail. Today I decided to test Mavericks Mail with a new Gmail account without using any of the known workarounds we have used in the past to get Gmail to work correctly with our email clients, I selected default settings in Mail and the following settings in Gmail > Settings in my browser. Surprise! It all just worked as expected.

Result:

  • No root folder required.
  • No prefix [Gmail]/ for custom folders.
  • I no longer had to assign folders under Mailbox >  “Use this folder for Drafts, Sent, Junk, Trash”.
  • When I deleted a message it actually went to Trash not to All Mail.

Gmail Browser Settings

IMAP-settings

Labels

It’s important that you select the All Mail folder. I know for many users this is an issue, but Mavericks Mail seems to require this setting. You might want to clean up the Label in the lower section. Many will be duplicates and/or empty. I would delete or remove.

labels

Mail creates the All Mail folder under Archive

archive

Tip: When setting up Gmail account in Mail, be sure to put your full email address as User in both the account window and in SMTP settings under the Advanced tab.

If you use Outlook for Mac, see Connect Outlook for Mac 2011 to Gmail’s IMAP service

 

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Use Search in Apple Mail

Mail uses tokens. From, To, Date, Contains etc are called tokens. More Info under Smart Search

I find that trying to enter multiple tokens in the “Find” box is difficult to see and manage since the search box fails to expand. For complex searches, follow these steps. This will bring up a search that is easier to use. For Entourage & Outlook users this should look more familiar.

1) Enter the person’s name. Select From, To or Entire Message. (you can enter any criteria to get started)  Alternatively, select New Smart Mailbox under Mailbox in the Menu bar.

2) Click on Save. I find this window to be easier to customize.

Continue clicking on the + to add criteria.

This last part is where Mail is not as elegant as Entourage or Outlook. You don’t see results without saving. This results in a smart folder added to the folder list.

If you decide to keep the smart folder,  you might want to create a template so the name is generic rather than a person’s name.

I used from criteria so it would not come up with any results for the template and the name would be search for my sidebar smart folder name.

Entering the from name field does not bring up results like the top search box so you would need the correct spelling for name.

 

To create a new search select to Edit Search by Control-Click (Right-click) on the Smart folder or select Mailbox in the Menu bar > Edit Smart Mailbox…

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