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.

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.

MailTips: Oversize Message

Scenario

The Oversize Message MailTip is displayed if the message the sender is composing is larger than configured message size limits in your organization.

The MailTip is displayed if the message size violates one of the following size restrictions:

• Maximum send size setting on the sender’s mailbox
• Maximum receive size setting on the recipient’s mailbox
• Maximum message size restriction for the organization
• Maximum Request Length setting (for Outlook Web App only)

Note:

Due to the complexity of the implementation, the message size limits on the connectors in your organization aren’t taken into account.

Note:

This MailTip isn’t displayed in Outlook Web App.

The screen shot below shows the wording for the MailTip when a users message size, for sending, is exceeded. For the purposes of this screen shot the limit has been set to 10KB.

The same MailTip wording is used if the message size exceeds the limit set for the organization, as opposed to a specific user. This means you cannot tell from the MailTip alone whether the limit is being imposed at the organizational level, or on you as a specific user.

The last screen shot is the wording for the MailTip when the message size limitation is applied on the recipient. In this case as you can see from the MailTip it tells you which recipient will not receive the email, because the message is to large.