Duplicate emails in Sent folder when using Outlook client with Gmail Account

When sending emails from my Outlook 2010 client, using my Gmail account, I would get duplicated entries in the ‘Sent Mail’ folder. This is been happening for some time but I’ve never gotten around to looking in to it.

Well, that’s just changed. I sent a friend an email and noticed it to was duplicated in my Gmail ‘Sent Mail’ folder so I started to look around, using what else but Google Search.

There are a number of entries out their dealing with duplicated emails in Gmail, a number of them from a few years ago. Then I found an entry that seemed to be more on point, that of using an Outlook client. So just to clarify, the scenario is this;

• Outlook 2010 client
• Outlook client using IMAP/SMTP connection to my Gmail account
• Send email from Outlook client using Gmail account
• Duplicate emails appear in Sent Mail folder

When I looked at the Internet headers for each of the duplicated emails there was a difference but as it happens I didn’t use this to identify and resolve the issue.

Instead, by doing a Google Search I found this entry; Problems sending mail, from Google themselves. Specifically the section Seeing duplicate Sent messages? which led me to Recommended IMAP client settings.

Looking at the various clients that Google has recommendations for I didn’t see Outlook 2010 so I just had a read of the general rule, specifically;

Sending:

• Do NOT save sent messages on the server. If your client is sending mail through Gmail’s SMTP server, your sent messages will be automatically copied to the [Gmail]/Sent Mail folder.

So I went in to the Account settings in Outlook and selected my Gmail account and clicked on ‘Change’. There’s a screen shot below of what you’ll see, for Outlook 2010. Click on the ‘More Settings …’ button.

Once the Internet E-mail Settings dialog box appears click on the ‘Sent Items’ tab and then click on the ‘Do not save copies of sent items’ radio button, as shown below.

This solved my duplicate emails in the Sent Mail folder. Now I only get a single copy of the email in the sent folder.

Microsoft Exchange, Outlook, Internet email accounts and Message Size Limitations

Background:

I have a Microsoft Exchange server at home that I use to familiarize myself with the various features and functions of Microsoft Exchange. I recently used this system to look at the Exchange MailTips functionality. This included the MailTip on Oversized Messages. To investigate this particular MailTip I set message limitations on specific mailboxes for both sending and receiving as well as setting a message size limitation at the Organization level. The post on Oversized Messages shows screen shots of each of these MailTips.

Scenario:

I use the Outlook 2010 client not just for my home Exchange server mailbox but also for the various Internet email accounts that I have. These include both POP3 and IMAP accounts. When I was investigating the Oversized Message MailTips I left in place the message size limitation at the Organization level. When I went to send an email, via Outlook, using one of my POP3 accounts I received a popup message to the effect that my message was to large, see below;

Note that this is not a MailTip but an Outlook Popup.

Implications:

This would seem to imply that the Exchange/Outlook configuration has an impact on any additional Accounts that you might have setup on your Outlook client.

Resolution:

The resolution to this issue was fairly easy, although I did run in to an ‘issue’. All I had to do was reinstate  the Organization message size limitation back to the default of 10MB, from the 10KB that I’d set it to. I did this via the Exchange Management Console. I’ve included a screen shots below. The first is where to set the global Send/Receive message size limitations. The second is the actual Properties dialog box.

 

 

Having re-set the message size limits I applied the changes and then went back to Outlook to re-try my email, with an attachment greater than 10KB. Unfortunately I still received the popup to the effect that the message was to large. This is the ‘issue’ that I ran in to.

I then stopped an re-started Outlook, on the basis that the change I’d made to Exchange hadn’t made its way down to my Outlook client and that by re-starting Outlook I would force the change to take effect, only it didn’t. I still received the popup.

I then went back to the Exchange server and re-booted it. yes, this is a brute force approach. It’s entirely possible that I could have just stopped and restarted the appropriate Exchange services. Or, it might be that the change would have take effect if I ‘d just waited, question is how long would I have had to wait.

Having re-booted Exchange Outlook still gave me the popup until I’d once again re-started Outlook, after the Exchange re-boot. At which time the restored message size limitations seemed to have taken effect on both Exchange and my Outlook client.

Conclusion:

That there are various Exchange configuration settings that impact Internet email accounts that you’ve configured in Outlook. In this particular case it does seem a bit od that a message size limitation set on Exchange is impacting an Internet email, POP3, account. One wonders what other Exchange configuration settings get applied to Internet email Accounts in Outlook?

Commentary:

I suppose the rational behind applying this particular configuration setting could be that if a company has imposed message size limitations on their internal email system then why shouldn’t they be applied to any other email system that’s using the companies infrastructure. One wonders though what happens when the user is not connected to the company network, that is they’re at home, on the road. Does the limitations still apply. Guess I’ll have to look in to this one.

MailTips: Custom, use of HTML

With Custom MailTips you can use HTML codes, well the <A href=> code, as part of the MailTip. However, I’ve only been able to see the HTML work when using Outlook Web Access (OWA). As you can see from the two screen shots below OWA displays the correct HTML but the Outlook client doesn’t.

This would seem to be a fairly useless MailTip capability as the OWA version of the MailTip would behave differently than the Outlook version. Seems that the only time when this capability would be of any real use would be in an environment where only OWA is used, or where you know that the Custom MailTip will only apply to OWA users.

In the example below I used the HTML code; ‘Please visit the Help Desk site  <A href = http://help-desk-support.companyname.com>&#160; to log a support call.</A>’

You could have also used similar HTML to send an email instead, as in; ‘Please contact me via email <A href=  "Mailto: john.doe@companyname.com"> at john.doe@companyname.com.</A>

In this later case instead of opening the targeted help desk web site an email will be opened with the email address pre-populated.

 

MailTips: Restricted Recipient

Scenario

The Restricted Recipient MailTip is displayed if the sender adds a recipient for which delivery restrictions are configured prohibiting this sender from sending messages.

The MailTip indicates the recipient to which the sender isn’t allowed to send messages and gives the sender the option to remove the recipient from the message. It also clearly informs the sender that the message won’t be delivered if sent.

If the restricted recipient is an external recipient, or if it’s a distribution group that contains external recipients, this information is also provided to the sender. However, the following MailTips, if applicable, are suppressed:

• Automatic Replies
• Mailbox Full
• Custom MailTip
• Moderated Recipient
• Oversize Message

The screen shot below shows the actual MailTip wording that you’ll see, for an Internal recipient.

The screen shot below shows the same wording for the MailTip in the case of a restricted External Recipient. In this case the External Recipient MailTip is also turned on so you get both the Restricted Recipient MailTip and the External Recipient MailTip.

MailTips: Reply-All on BCC

This MailTip is only supported in Microsoft Office Outlook Web App. It does not show up when using Outlook.

The Reply-All on Bcc MailTip is displayed if the sender receives a Bcc copy of a message and selects Reply to All.

When a user selects Reply to All to such a message, the fact that the user received a Bcc of that message is revealed to the rest of the audience to which the message was sent. In almost all cases, this is an undesirable situation, and this MailTip informs the user of this condition.

The screen shot below shows the wording you’ll see for this MailTip.

 

Note:

This MailTip is only supported in Microsoft Office Outlook Web App.