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Naughty Outlook

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Naughty Outlook
Testing Outlook 2003
Testing Outlook 2007
Testing Outlook 2010
Sample emails
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Before you set up Easy-Email synchronization for Outlook, there is one issue that we want to be sure you know about.

We refer to it as “Naughty Outlook” because Outlook sends emails on your behalf without asking your permission and quite frankly we think that's a bit naughty! And it is something Microsoft has known about since 2007 and hasn't fixed which makes it a Double Naughty...

It's not in all versions of Outlook and it only affects emails requesting read receipts so it may not ever be an issue for you. A full discussion of this issue - and the potential solutions – is outlined below.

Fortunately it looks as if Outlook 2010 does not suffer from this problem.

You can download a PDF version of this article here.

The bug

When someone sends an email they can ask for a 'Read Receipt'. This is an email which is sent back to the sender of the email, so this person can see that their email has been read.

By default Outlook will ask you for permission before it sends the 'Read Receipt' so you can choose not to send it. However there is a bug in Outlook so sometimes it sends the 'Read Receipt' without asking you.

Microsoft has acknowledged this problem and opened a bug report on 28 December 2007, but a fix has not been provided yet.

When does this happen?

The bug is triggered when you work with your email using the IMAP protocol (which Easy-Email does) and you manage your email from more than one computer, for instance Outlook on your home computer and on your office computer.

An example:

You download an email on your office computer and then go home without reading it. At home you download the same email to your home computer, read it and move it from the inbox to another folder.

When you get back to the office and start up Outlook on your office computer it gets confused because the email is no longer in the inbox, and it will send an email to the sender saying the email has been deleted without being read.

This only happens for emails where a 'Read Receipt' has been requested.

Which versions of Outlook are affected?

Some versions of Outlook 2003 and 2007 are affected and some are not (yes, there are different build versions), so you will have to test to know for sure.

Initial tests with Outlook 2010 show that it is not affected by this problem, but we do recommend that you test to make sure the problem does not come back in later releases.

We have not tested Outlook XP and Outlook 2000.

Your choices

First you need to test your Outlook.

If you do not have a Naughty Outlook: Go ahead and set up Easy-Email.
If you do have a Naughty Outlook but nobody sends you emails with read receipts: Go ahead with Easy-Email.
- In this case we recommend that you turn off the Outlook Junk Mail handling and hide the Gmail Spam folder from IMAP using the Gmail lab feature “Advanced IMAP Controls”.
If you have a Naughty Outlook and do not want any Read Receipts to go out your options are:
- Upgrade to Outlook 2010 (test first with the trial version).
- Change to Thunderbird.
- Don't synchronize your email using Easy-Email.
  If you have already bought the guide you can use our Money Back Guarantee to get a refund.

Links to related articles

We have gathered a few resources on the internet which discuss this problem.

Microsoft Developer Network posting with the bug report:

http://social.msdn.microsoft.com/forums/en-US/innovateonoffice/thread/82024df4-d5ec-4f89-b268-f824dc26c370/

A thread on EmailDiscussions.com:

http://www.emaildiscussions.com/showthread.php?t=51114

A thread on slipstick.com:

http://www.slipstick.com/problems/rr_ndr.asp

Follow these instructions to test Outlook 2003:

If you need more detailed instructions for setting up Gmail and Outlook please read chapter 6 and 7 in the Essential Guide, which you can download here.

If you do not already have a Gmail account create one. It's free.
Enable IMAP on your Gmail account.
- Go to Settings → Forwarding and POP/IMAP.
- Enable IMAP and Save Changes.
In Outlook add a new account to connect to your Gmail.
- Go to Tools → Email Accounts
- Choose Add a new e-mail account and click Next.
- Choose IMAP and click Next.
- Enter a name.
- For E-mail Address enter your Gmail address.
- For incoming mail server enter: imap.gmail.com
- For outgoing mail server enter: smtp.gmail.com
- For Login Information enter:
  - Enter your full Gmail address as User Name
  - Enter your Gmail password.
- Click More settings
  - On the Outgoing Server tab tick My outgoing server requires authentication.
  - On the Advanced tab tick both boxes This server requires an encrypted connection (SSL).
  - Change the Outgoing server port to 465.
  - Click OK then click Next and then Finish
- From the main Outlook window go to Tools → Options...
  - Click the Mail Setup tab.
  - Click the Send/Receive button.
  - Click the Edit button.
  - Select your gmail account on the left hand side, then click on the Inbox and select Download complete item including attachments.
- Return to the main Outlook window.
Send an email from Outlook to your Gmail account requesting a 'Read Receipt'
- Click New.
- Send the email to your gmail address.
- Click the Account button and select your gmail address to send the email from.
  The account button is only visible if you have more than one account in Outlook.
- Ask for a Read Receipt. To do this click Options.
  Then tick Request a read receipt for this message.
- Send the email and wait for it to appear in your inbox.
  Do not open or read the email.
- If there is a small white icon next to the email click Send/Receive to download the complete email.
- Close Outlook.
- Log on to Gmail via a web browser.
- Delete the email you just sent.
- Start Outlook again. Wait for the automatic Send/Receive to complete.
  You can see the status in the lower right hand corner.
- Restart Outlook.
- If you have a Naughty Outlook you will now see an email like this in your inbox:

Follow these instructions to test Outlook 2007:

If you need more detailed instructions for setting up Gmail and Outlook please read chapter 6 and 7 in the Essential Guide, which you can download here.

If you do not already have a Gmail account create one. It's free.
Enable IMAP on your Gmail account.
- Go to Settings → Forwarding and POP/IMAP.
- Enable IMAP and Save Changes.
In Outlook create a new account to connect to your Gmail.
- Go to Tools → Account Settings.
- Tick Manually configure server settings or additional server types and click Next.
- Leave Internet E-mail selected and click Next.
- For E-mail Address enter your Gmail address.
- Choose IMAP as account type.
- For incoming mail server enter: imap.gmail.com
- For outgoing mail server enter: smtp.gmail.com
- For Login Information:
  - Enter your full Gmail address as User Name.
  - Enter your Gmail password.
- Click More settings
  - On the Outgoing Server tab tick My outgoing server requires authentication.
  - On the Advanced tab:
    - For both boxes with Use the following type of encrypted connection choose SSL.
    - Change the Outgoing server port to 465.
  - Click OK then click Next and then Finish.
Send an email from Outlook to your Gmail account requesting a 'Read Receipt'
- Click New.
- Send the email to your gmail address.
- Click the Account button and select your gmail address to send the email from.
- Ask for a Read Receipt. To do this click the little arrow next to Options.
  Then tick Request a read receipt for this message.
- Send the email and wait for it to appear in your inbox.
  Do not open or read the email.
- Close Outlook.
- Log on to Gmail via a web browser.
- Delete the email you just sent.
- Start Outlook again. Wait for the automatic Send/Receive to complete.
  You can see the status in the lower right hand corner.
- Restart Outlook.
- If you have a Naughty Outlook you will now see an email like this in your inbox:

Follow these instructions to test Outlook 2010:

If you do not already have a Gmail account create one. It's free.
Enable IMAP on your Gmail account.
- Go to Settings → Forwarding and POP/IMAP.
- Enable IMAP and Save Changes.
In Outlook create a new account to connect to your Gmail.
- Click the File tab in the top left hand corner.
- Go to Add Account.
- Enter a name.
- For E-mail Address enter your Gmail address.
- Enter your Gmail password twice.
- Click Next.
- Outlook finds your settings automatically. Click Finish.
Send an email from Outlook to your Gmail account requesting a 'Read Receipt'
- Click New E-mail.
- Send the email to your gmail address.
- Click the From button and select your gmail address to send the email from.
- Ask for a Read Receipt. To do this click the little arrow below Low Importance.
  Then tick Request a read receipt for this message.
- Send the email and wait for it to appear in your inbox.
  Do not open or read the email.
- If your email has a little white icon next to it you need to click Send/Receive to download the full email.
- Close Outlook.
- Log on to Gmail via a web browser.
- Delete the email you just sent.
- Start Outlook again. Wait for the automatic Send/Receive to complete.
  You can see the status in the lower right hand corner.
- At this point you might be prompted if you wish to send a Read Recipt.
  If this happens select No.
  If you do not want to send Read Receipts at all tick Don't ask me about sending receipts again.
- Restart Outlook.
- If you have a Naughty Outlook you will now see an email like this in your inbox:
  (The email shown here was sent by an Outlook 2007)