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.

This copy of the Install OS X Yosemite application can’t be verified. It may have been corrupted or tampered with during downloading.

If you are trying to use an installer you downloaded previously…

OS X installers downloaded prior to 14 February 2016 won’t work- See TidBITS article: Previously Downloaded OS X Installers No Longer Work [Added 02 Mar 2016]

Trying to update a client’s computer today. After downloading Yosemite installer it failed to run. It would start but fail with the following error:

This copy of the Install OS X Yosemite application can’t be verified. It may have been corrupted or tampered with during downloading.

First step was to download again. That failed. Tried downloading again. Failed. Started looking for help and found many suggestions that worked for some users. After trying reset date, repair permissions, repair drive, remove RAM and downloading multiple times, user purchased a USB thumb drive and we were able to create a bootable OS 10.10 Yosemite installer drive using the installer that failed to run.

  1. The Install Mac OS X Yosemite.app must be in Applications.
  2. Format the USB drive as GUID in Disk Utility. 8GB or larger
  3. Name “Untitled”
  4. Paste the following into the Terminal
  5. Enter Password
  6. When the process is finished you will see Copy Complete. Done. (the process took about 30 min so be patient)
  7. Select the drive in System Preferences > Startup Disk to install.

Thanks to Dan Frakes for instructions on creating USB installer. For more details, see Dan’s blog:

http://danfrakes.com/2014/10/16/how-to-make-a-bootable-yosemite-installer-drive/

[Added info: December 3, 2015] Check out the FAQs on DiskMaker X page for help with errors making a boot disk. DiskMaker X is a free app that many find useful in creating a bootable install disk. This can be very helpful if you are running El Capitan and want to install an older version of OS X like Yosemite on another drive.

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

Search include System Files and Invisible Files

Searching for data that you can’t find in a regular Spotlight search? Add System Files and Invisible files to your search.

search_kind...

How To Create Search

Click on the Desktop so the Finder is active. You’ll see Finder listed by the Apple in the Menu bar.

Finder

Command F will create a new search window.

Finder.

Select Other

search_kind

Add System Files

search_kind.

Add File Invisiblesearch_kind..

File visibility > Visible or Invisible

search_kind...

Create an OS X Mavericks Partition

If you are unhappy with your upgrade to Mavericks, you can eliminate any issues installing over your old software by creating a partition on your drive or external drive to install a clean version of Mavericks for testing. The base install will quickly tell you if you will see a speed difference or if issues you were seeing are a result of old files that are conflicting with Mavericks.

  1. Open Disk Utility in Applications/Utilities.
  2. Select your drive in the left window.
  3. Name the new partition “Mavericks HD”. See below on how to determine size.
  4. Apply will modify the current partition table to add the new partition.

How to determine size of partition

You could make this partition as small as 30GB, but more is better. If you have the room and plan on moving all your data to this partition, first find how much space is currently used.

In this first example, I have a 160 GB drive with approx 49 GB used. I have 110 GB available so I have plenty of room to create a partition that is equal in size and still leave some breathing room on the first partition to run OS X. (You need a minimum of 10% free.)

DiskUtility

  • Click on the drive – top name not Macintosh HD
  • Click on Partition tab
  • Click on + to add a second equal partition.
  • Rename Partiton – Mavericks HD (It’s easy to change later if desired)
  • Select Apply

(until you click on Apply, you can make changes.)
DiskUtility.

Not enough free space on drive?

This next example is for users that don’t have enough free disk space to make a full restore Mavericks drive. You can install Mavericks with a little room to spare for testing some files on a 30 GB partition. Make the partition as large as possible while still leaving some room for the other drive to boot. It’s recommended that you have 10% free for the system to “breathe”.

Follow the same steps as above but this time, drag down the center bar, to resize the bottom partition. This shows a 30 GB partition.

Click on Apply to create the partition.

DiskUtility..

Install Mavericks

Download Mavericks installer from Mac App Store (MAS). If you have previously downloaded, go to Purchases tab in the MAS and select to download again.

purchases

Put your cursor over OS X Mavericks (you will see the cursor turn into a hand. Click and it will take you to the download page.

purchases..

The installer can be found in the Applications folder called Install Mac OS X Mavericks. Launch the installer and select your new Mavericks partition as destination.

The next post will describe how to move over your data without using Migration.

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

 

How to enable User’s Library folder

Starting with Lion, you’ll need to enable the User’s Library folder in order to make any changes in your User’s Library/Preferences.

Option 1)

Select the Finder in the Dock. Under Go in the Menu bar > hold down the Option key and you’ll see the Library.

ShowLibraryOptionKey

Option 2)

Open the Terminal and type

chflags nohidden /Users/[username]/Library/

Return key to activate

Option 3)  

Starting with Mavericks, Apple gave us a new option to turn on the User’s Library folder.

To toggle this option on, simply open a new Finder window and go to your home folder. Then press Command-J or choose “Show View Options” from the View menu. When done, you should see an option to “Show Library Folder” among other view options, which can be checked to reveal the Library folder.

ShowLibrary.

 

 

ShowLibrary

Use OS X Recovery Disk Assistant to reset Your files and folder permissions

OS X Recovery Disk Assistant

  • Disk Utility in Applications/Utilities lets you verify and repair Mac OS X disks and permissions issues.
  • The Recovery drive has an additional Repair Permissions application utility hidden away. This allows you to repair permissions on YOUR files and folders.
    • This tool is located inside boot Repair Utilities.

We are going to use this option to repair permissions on your files and folders. After restarting your entire drive will be re-indexed by Spotlight.

  • Outlook users that are having difficulty with search even after re-indexing and creating a new Identity can use this option to fix search for their Identity.
  • Your Outlook identity opens without saving previous data.
  • Spotlight fails to index your files and folders.

Restart and hold down the Command and R keys during start-up to boot into the Recovery Disk Assistant. (This is a new feature for Lion/Mountain Lion/ Mavericks. Not an option for Snow Leopard)

You will boot into the Repair Utilities screen. On top, in the Menu Bar click the Utilities item then select Terminal.

Recovery

 

 

In the Terminal window, type resetpassword and hit Return.

terminal

 

 

 

The Password reset utility launches, but you’re not going to reset the password.

  1. Select your startup volume at the top
  2. From the dropdown below it, select the user account with the problem.
  3. At the bottom of the window, you’ll see an area labeled ‘Reset Home Directory Permissions and ACLs’. Click the Reset button there.The reset process only takes a couple of minutes. It’s not obvious when it’s finished.
  4. Quit Reset Password
  5. Quit Terminal
  6. Quit OS X Utilities and restart your Mac. **

**While booted from the Repair drive, you can run Disk Utility to check or repair your hard drive. I suggest running Repair Drive while booted from the Recovery drive.

After you restart your entire hard drive will re-index. Depending on the size of your drive, this can take hours. Until this process is finished, Spotlight won’t know the contents of your disks and neither will Outlook. All lists like contacts, events, notes etc. are generated by the Spotlight searches.

Note: You can tell if Spotlight is still in progress by simply looking at the Spotlight menu: There’s a blinking dot in the middle of the magnifying glass while indexing is occurring. You can also open Activity Monitor in Applications/Utilities and type in md in the search filter. You should see mdworker32 and mdworker. The file, mdworker32 is for Outlook and mdworker is for system.

How to partition an external drive using Disk Utility

Outlook users that need to rebuild their Identities that do not have enough free space on their internal drives will need to use an external drive with enough free space for the rebuild.  I recommend a minimum of 300 GB free.

If you purchase a new drive, be sure to format it first using Disk Utility as Mac OS X Journaled. The drive must be formatted as GUID Partition Table to be bootable. I would not partition and use the entire new drive for the rebuild. You can always add a partition if needed after you complete the rebuild.

If you have an external drive that already has files on it but does have enough free space, use these steps to add a partition for the rebuild.

Using Disk Utility, select your external drive and add the largest partition available. I suggest a minimum of 300GB free.

  • Open Disk Utility
  • Select the disk where you want to create a new partition and click Partition
  • Select an existing partition in the Volume Scheme list, and click Add (+). Disk Utility splits the partition into two, leaving the data from that partition in one of the new partitions. If the partition is less than half-full, Disk Utility creates two partitions of equal size. Otherwise, it creates one partition large enough for the data, and another partition with the remaining space.
  • Resize the partitions as needed. You can drag the dividers between the partitions in the Volume Scheme list, or you can select a partition in the Volume Scheme list, and then enter a value in the Size field.
  • If this drive has never been used, choose a format. Select a filesystem type (Mac OS Extended Journaled is default). The drive must be formatted as GUID Partition Table to be bootable.
  • Click Apply.
  • See Disk Utility Help for additional info.

When I made my recovery partition, I used my Seagate 2TB that holds my clone backups for old OS X installs. I added a partition by selecting the bottom partition “Virtual” by clicking on the + sign.  If you no longer wish to keep this partition after recovering, you can remove and give the space back to the drive.