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Q: I have a Dell Inspiron laptop running Windows 10 Home, version 1803. Our ISP is Cox.com. We have MS Office 2016 installed on the PC and use Outlook for our e-mail. Up until about a month ago my wife and I were not having any problems with Outlook. Then we started getting a message that my wife’s e-mail wasn’t getting through to Outlook any more. My personal Outlook is still working perfectly fine. When we launch Outlook for my wife we receive a message from an Outlook Send/Receive Progress pop-up that states “Reported error (0x800CCC0E): Outlook cannot synchronize subscribed folders for xxxxxx@cox.net. Error: Cannot connect to the server. Contact your server administrator or ISP.” I have looked at the settings at our e-mail accounts and they are the same. The ISP (Cox) said the problem was with MS Windows and they must be contacted to fix the problem. I have tried a number of fixes recommended on-line with no success. My Outlook e-mail continues to work fine. My wife has started to use Cox E-mail instead. I tried synchronizing my wife’s account under Windows and it states “Sync is not available for your account. Contact your system administrator to resolve this.” I am my system’s administrator. I didn’t change any account settings on my wife’s account to all at once create this problem so I don’t know what to do. Help me get her back to using Outlook please.

– Ron H.
Shalimar, Florida

A: I’ll do what I can, Ron, but in my opinion, there’s an awful lot to be said for using your provider’s webmail interface. Except for e-mail at my main employer, I use webmail exclusively for the multiple e-mail accounts that I manage, which includes my personal address, two for this column, one for my Christmas light show, and one for a small business I operate. I’ve even gotten Spouse Peripheral to use webmail, and she’s been perfectly happy with it since she got used to it. Unlike various e-mail clients, webmail always works correctly. I don’t need to worry about updates, or the company withdrawing support for it, or trying to force me to upgrade. And I don’t get weird errors where something appears to work on one machine, but not on another, identically configured machine.

 I’ll also say that I strongly disagree with the way Cox chose to handle your issue. Or should I say, the way they chose not to handle it. Regular readers of this column have seen this as a recurring pattern. When it comes to Cox, it seems like it’s always someone else’s fault, and they just aren’t willing to work with their customers to resolve issues – even those that directly affect the use of their products. They have some work to do on their customer service in this Geek’s opinion.

From what I can tell by researching your problem (thank-you for including such detailed error messages, by the way) this problem is not being caused by e-mail account mis-configuration, which is probably why you can’t find any differences in the settings between the two accounts.

What is probably standing in the way of your folders synchronizing are security settings. Specifically, something called Transport Layer Security (TLS) and Secure Sockets Layer (SSL). These are cryptographic protocols, intended to secure the communication between two points on the Internet, so that no third party can tap into the stream of data. SSL is older, dating back to 1999. It is deprecated and replaced by TLS, the current version of which was finalized in 2018.

What probably happened is that some security update inadvertently changed the settings on one of your computers. You can change them back, or rather; change the non-working one to match the working one. You’ll find these settings by performing the following steps: Click the Windows Start button and in the search box, type “Internet Options”. Click the corresponding entry in the search results. You’ll receive a dialog labeled “Internet Properties” (not “Options” – Thanks, Bill). Go to the “Advanced” tab and scroll all the way to the bottom. A few lines up, you’ll find entries for using SSL and various versions of TLS. My preferred configuration is for SSL to be unchecked, and all of the TLS versions to be checked. However, in your case, since you have a working model, set up the non-working one to match it.

There is a possibility that you may be using certain antivirus/antispyware software that also has SSL/TLS settings that could also be causing this problem. One example is ESET NOD32. It has an option to perform TLS/SSL filtering, which should be disabled if your e-mail configuration uses IMAP. Good luck – and give serious consideration to switching off e-mail clients altogether, and just using webmail!