Office365 / Outlook 2013 / Outbox / Disconnection Issue

We have a network using Office365 with Outlook 2013. Each user on the network is having intermittent connectivity issues.

Outlook always says it's connected. We notice the issue when we try to send an e-mail and it just sits in the Outbox. We also do not receive any e-mails.

To fix, we shutdown Outlook, re-open, and the items in the Outbox are sent and we receive e-mail. Outlook will work for a few hours, even days, and then the issue returns. There is no way to know the issue is even happening until our sent e-mails start sticking in our outbox.

Any ideas? We passed all of the Outlook365 prerequisites on each of the PCs. The network is very small with less than 10 PCs and no server. Our firewall is a Cisco RV180 with a Cisco SG300 switch.
qualityipAsked:
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JohnBusiness Consultant (Owner)Commented:
When you try to receive an email, and it does not receive, Outlook should give you an error in the lower right corner.

Also expand the Send/Receive detail window. What error is given?  This will be the key error to look at.
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Alan HardistyCo-OwnerCommented:
Are you up-to-date with Windows / Office Updates?

Have you disabled PowerSave on the Network Card / Wireless Network card(a)?  If not, please do.

To do this click on Start> {type} ncpa.cpl {press enter} > Right-Click the Network / Wireless Network Card and choose Properties.

On the next window, click the Configure button.

Select the Power Management tab and untick everything from the bottom up then Apply / OK and close all open windows.

Monitor for problems.

Alan
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qualityipAuthor Commented:
This is what we've tried so far:

Disabled Outlook add-ins
Created new Outlook profiles
Re-installed Outlook 2013
Replaced old Netgear switch with Cisco SG300
Disabled power save settings on NICs
Ran ping test for a day to confirm stable connectivity to Internet
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qualityipAuthor Commented:
We are fully up to date with Windows/Office updates. Our router has the latest firmware.
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JohnBusiness Consultant (Owner)Commented:
When you do Send / Receive, what does the Dialogue Box show? Remember to Show Details.
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qualityipAuthor Commented:
The issue just happened so I opened the connection status and send receive details. In the background, you can see the message sitting in the Outbox. Outlook will stay like this until we close and re-open.
outlook-error.PNG
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qualityipAuthor Commented:
Ah, just noticed details weren't shown in my screenshot, let me check again.
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JohnBusiness Consultant (Owner)Commented:
At this point, the screen says Outlook may be having issues with sending. It is feasible your ISP changed Port number and SSL rules. They could be in transition, so this is another thing to check. You need to know what your ISP wants now.
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qualityipAuthor Commented:
That's interesting about the SSL rules, because we receive these two errors on the PCs.

Log Name:      System
Source:        Schannel
Date:          2/24/2014 8:33:49 AM
Event ID:      36888
Task Category: None
Level:         Error
Keywords:      
User:          SYSTEM
Computer:      rc-01-dt-13
Description:
The following fatal alert was generated: 40. The internal error state is 107.





Log Name:      System
Source:        Schannel
Date:          2/24/2014 8:33:49 AM
Event ID:      36874
Task Category: None
Level:         Error
Keywords:      
User:          SYSTEM
Computer:      rc-01-dt-13
Description:
An SSL 3.0 connection request was received from a remote client application, but none of the cipher suites supported by the client application are supported by the server. The SSL connection request has failed.
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JohnBusiness Consultant (Owner)Commented:
It would seem to be having an issue with your routers. I use a Cisco RV220W router in my Home Office and do not have issues.

Can you check the sending with just the router and not the switch?  Can you upgrade the firmware on the RV180?
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qualityipAuthor Commented:
Yes - we actually had one PC connected to the router and one PC connected to the Cisco SG switch and both PCs had the issue.
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JohnBusiness Consultant (Owner)Commented:
I think I would be inclined to open a case with your ISP. What you have is not normal, and I am not seeing any issue with almost the same gear (Outlook 2013, Cisco RV220W router).
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qualityipAuthor Commented:
Our ISP is Time Warner Cable and we have several hundred other users on different domains with the same Internet service that do not have the same issue.
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JohnBusiness Consultant (Owner)Commented:
Strange. Consider getting a decent spare switch and replace the Cisco switch with the replacement switch. You imply in the first post that you had the RV180 plus a Netgear switch and the issue occurred after replacing the Netgear with the Cisco switch.

Outlook is usually happy with most switchgear but I am not sure what else.
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qualityipAuthor Commented:
The issue was occuring with the original Netgear switch. That's why we replaced the Netgear switch with the Cisco SG300 switch in the first place.

It just happened again! Third time today. Office365 is killing me. At least opening and closing Outlook is an easy fix.

Kind of interesting. We know when we get e-mails when the issue is happening because our cell phones (which are connected to the wifi) receive an e-mail but the e-mail does not show up in Outlook. Then, we close and re-open Outlook and the e-mail is there.
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JohnBusiness Consultant (Owner)Commented:
I set my own iPhone to a static IP on my home office network because it was using the PC IP address forcing the PC to change. I am not sure why the iPhone was taking priority but it did. So I move the addressing to a different range. Outlook was not affected but the computer was.

See if the iPhone can use a different IP range.
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qualityipAuthor Commented:
That error is concerning and could be causing the issues. What does it mean that none of the cipher suites that are supported by the client are supported on the server? I know Office365 uses HTTPS


Log Name:      System
Source:        Schannel
Date:          2/24/2014 8:33:49 AM
Event ID:      36874
Task Category: None
Level:         Error
Keywords:      
User:          SYSTEM
Computer:      rc-01-dt-13
Description:
An SSL 3.0 connection request was received from a remote client application, but none of the cipher suites supported by the client application are supported by the server. The SSL connection request has failed.
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JohnBusiness Consultant (Owner)Commented:
For outgoing mail, I use port 587 / TLS.  SSL did not work with my email provider (who I know personally). But this information needs to come from your ISP. I mentioned that farther back.

If you have both incoming and outgoing port numbers and SSL settings correct, then your ISP needs to assist (as I think about it). Outlook 2013 does not yield such errors in a normal setup (I have been using Outlook 2013 for about a year now).
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qualityipAuthor Commented:
The Cisco RV router was the culprit. We replaced with a Meraki and have no issues.
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JohnBusiness Consultant (Owner)Commented:
@qualityip  - Thank you for the update and I was happy to help.
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