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When you delete a message, try Shift Delete to just delete the message directly. It is permanent so take care. <br />
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Can you empty the Deleted Items folders before syncing to IMAP occurs? &nbsp;Probably not but check.
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When you delete a message, try Shift Delete to just delete the message directly. It is permanent so take care.

Can you empty the Deleted Items folders before syncing to IMAP occurs?  Probably not but check.

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Yes, I just tested. Shift Delete prompts and then OK and it is gone (permanently) so will not sync the Deleted Item. Nothing in there.
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Yes, I just tested. Shift Delete prompts and then OK and it is gone (permanently) so will not sync the Deleted Item. Nothing in there.

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Alternatively setup a clean new mail profile, wait for it to finish syncing, and delete a message. Could be that the ost or pst is corrupt.
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Alternatively setup a clean new mail profile, wait for it to finish syncing, and delete a message. Could be that the ost or pst is corrupt.

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are you sure you are syncing to the inbox in gmail and not the 'all mail' box?
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are you sure you are syncing to the inbox in gmail and not the 'all mail' box?

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It's not &quot;all mail&quot;. &nbsp; I deleted all messages containing the keyword phrase &quot;nextdoor&quot; and &quot;godaddy&quot; earlier. &nbsp; I have since did a ctrl A to select all messages in &quot;trash&quot; &nbsp; &nbsp;Unfortunately, it repopulates there as well. &nbsp;I will create a separate profile in Outlook to see if there's an alternative outcome.
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It's not "all mail".   I deleted all messages containing the keyword phrase "nextdoor" and "godaddy" earlier.   I have since did a ctrl A to select all messages in "trash"    Unfortunately, it repopulates there as well.  I will create a separate profile in Outlook to see if there's an alternative outcome.

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Try resetting your rules as well.<br />
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Somewhere I read that there was a design change after Outlook 2007 to keep deleted items in IMAP folders. So I think your Outlook is working as designed.
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Try resetting your rules as well.

Somewhere I read that there was a design change after Outlook 2007 to keep deleted items in IMAP folders. So I think your Outlook is working as designed.

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Log into your gmail account, click on the Gear icon (top right) and go to Settings.<br />
<br />
Click on the IMAP tab and check the two options highlighted in the screen shot below:<br />
<br />
<a href="https://filedb.experts-exchange.com/incoming/2016/08_w32/1109624/gmail-imap.jpg" target="_blank" title="Gmail IMAP Settings (59 KB)"><img alt="Gmail IMAP Settings" class="file-block lazyload" style="max-width: 800px;" data-src="https://filedb.experts-exchange.com/incoming/2016/08_w32/800_1109624/gmail-imap.jpg" /></a>
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Log into your gmail account, click on the Gear icon (top right) and go to Settings.

Click on the IMAP tab and check the two options highlighted in the screen shot below:

Gmail IMAP Settingshttps://filedb.experts-exchange.com/incoming/2016/08_w32/1109624/gmail-imap.jpg

gmail-imap.jpg

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Two options are already highlighted. &nbsp;I created a new outlook profile. &nbsp; I'm still receiving the same results. &nbsp;This is for a client's Google Apps for Work. &nbsp;I have a very similar similar setup for my business and it works fine for me.
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Two options are already highlighted.  I created a new outlook profile.   I'm still receiving the same results.  This is for a client's Google Apps for Work.  I have a very similar similar setup for my business and it works fine for me.

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What version of Outlook are you using? &nbsp;Outlook 2013 doesn't seem to play nice with gmail. Outlook 2016 works a lot better. You mentioned you had a similar setup to your client - are you both using the same version of Outlook?<br />
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Can you check to see that there are any service pack or office updates?
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What version of Outlook are you using?  Outlook 2013 doesn't seem to play nice with gmail. Outlook 2016 works a lot better. You mentioned you had a similar setup to your client - are you both using the same version of Outlook?

Can you check to see that there are any service pack or office updates?

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Does your Advanced settings tab match this screen shot?<br />
<br />
<a href="https://filedb.experts-exchange.com/incoming/2016/08_w33/1110499/gmail_outlook_2013_image8.png" target="_blank" title="Outlook Advanced tab (88 KB)"><img alt="Outlook Advanced tab" class="file-block lazyload" style="max-width: 402px;" data-src="https://filedb.experts-exchange.com/incoming/2016/08_w33/1110499/gmail_outlook_2013_image8.png" /></a>
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Does your Advanced settings tab match this screen shot?

Outlook Advanced tabhttps://filedb.experts-exchange.com/incoming/2016/08_w33/1110499/gmail_outlook_2013_image8.png

gmail_outlook_2013_image8.png

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It's 2016 Outlook. &nbsp;Those settings in the pic are the same. &nbsp;Im downloading eM Client to see if the results differ.
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It's 2016 Outlook.  Those settings in the pic are the same.  Im downloading eM Client to see if the results differ.

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Did you try any of the recent suggestions including a new Windows User Account?
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Did you try any of the recent suggestions including a new Windows User Account?

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I have my assistant steadily deleting email/unsubscibing through the gmail web interface. &nbsp; It does not seem be a issue using an alternative to Outlook. &nbsp;eM Client works fine.
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I have my assistant steadily deleting email/unsubscibing through the gmail web interface.   It does not seem be a issue using an alternative to Outlook.  eM Client works fine.

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I will be migrating to Hosted Exchange later this week for other reasons. &nbsp;Regardless, this should fix everything. &nbsp;Thanks
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I will be migrating to Hosted Exchange later this week for other reasons.  Regardless, this should fix everything.  Thanks

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Thanks for the update and I was pleased to assist.
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Thanks for the update and I was pleased to assist.

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<div class="content wysiwyg-content">
Outlook uses IMAP with Google Apps. &nbsp;Messages that are deleted quickly sync back with Google mail server and repopulate the inbox with the &nbsp;deleted messages in the inbox.
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Outlook uses IMAP with Google Apps.  Messages that are deleted quickly sync back with Google mail server and repopulate the inbox with the  deleted messages in the inbox.

Deleted email messages repopulate in Outlook email account

Microsoft Outlook is a personal information manager from Microsoft, available as a part of the Microsoft Office suite. Although often used mainly as an email application, it also includes a calendar, task manager, contact manager, note-taker, journal, and web browser.

Outlook

Interactions between email servers and clients are governed by email protocols. The three most common email protocols are POP, IMAP and MAPI. Most email software operates under one of these (and many products support more than one).  The correct protocol must be selected, and correctly configured, if you want your email account to work.

Email Protocols

Within Internet message handling services (MHS), a message transfer agent or mail transfer agent (MTA) or mail relay is software that transfers electronic mail messages from one computer to another using a client–server application architecture. A MTA implements both the client (sending) and server (receiving) portions of the Simple Mail Transfer Protocol (SMTP). The terms mail server, mail exchanger, and MX host may also refer to a computer performing the MTA function. The Domain Name System (DNS) associates a mail server to a domain with mail exchanger (MX) resource records containing the domain name of a host providing MTA services.