Akrutosync iPhone to Outlook activity halted

 

For years, I have been using Akrutosync to sync Outlook calendar, contacts, tasks and notes on my Windows 10 PC running Norton Internet Security, with an iPhone, now running iOS 12.1.  This arrangement worked reliably until Tuesday 6 November about the middle of the day (in South Australia, GMT + 10.5 Summer Time).  After much troubleshooting with Akrutosync remote support, I arrived at the point where all the contacts, etc. had been removed from the iPhone and Akrutosync was reinstalled on the PC and still I could not restore the sync.  This is serious – I run my life on the Outlook/iPhone capability!

In my troubleshooting, I used Wireshark, ARP and netstat to investigate the traffic flow during the Akrutosync configuration phase when it uses a web server for an information exchange with the iPhone running Safari:

  1. A SYN packet comes into the PC from the iPhone
  2. The PC responds with a SYN, ACK
  3. The iPhone keeps sending SYN packets until the PC resets the connection.
  4. I only ever see a SYN_RECEIVED status for the iPhone on the PC’s netstat output

The above occurs whether the NIS Smart Firewall and Auto-Protect are disabled in the System Tray or not.

In other testing, I discovered that a MacBook Air and an iPad both with Safari, and a PC with Edge could all connect to the Akrutosync server, but neither my iPhone nor my wife’s could.

The Akrutosync guy and I concluded that some kind of firewall issue could be the problem.  To test this, I loaded Akrutosync on my Windows 10 notebook which uses Microsoft Defender rather than NIS and was able to complete the Akrutosync configuration flawlessly.  I have my life back but it is awkward running this Outlook to iPhone service via my notebook.  I don’t always have it in use and besides the Outlook environment is much easier to use on the big screen of the PC.

Can anyone explain how NIS could pick on iPhones in not completing a 3-way handshake while everything else I can lay my hands on seems to work OK?  Or, am I asking the wrong question?

Had you changed the Network Cost Awareness setting in the past? The default is Off.

If the default is Off then I guess I must have changed it.  I can't imagine why, though, and it was sufficiently long ago that I can't remember doing it.  I would rather leave NIS to do its thing while I get on with more interesting stuff.  What's pretty clear is that I hadn't changed the Network Cost Awareness last week when the problem arose with Akrutosync.  This is why I suspect iOS 12.1 has changed its behaviour in some way that isn't configurable by the user.

Thanks for your support on this problem.

Good find. Thanks for letting us know.

Had you changed the Network Cost Awareness setting in the past? The default is Off.

 

I noticed your figure showed the Network Cost Awareness in Network Settings was set to Off.  Mine was On on the PC.  I changed it to Off and the sync proceeded normally smiley

What security software is on the PC with Edge?

Defender.

Have you tried again on the affected PC? How did you disable the SmartFirewall and Auto Protect? From the right click of the Norton icon in the System tray?

Yes, I have tried a number of times on the affected PC.  Yes, I tried disabling SmartFirewall and Auto Protect in the System Tray.  At one stage I even had a permit any-to-any rule in the firewall.

Your diagnosis led you to feel it is a firewall issue.  To reset the Norton firewall, from the main Norton Security screen click on Settings - Firewall. On the General tab, click on Reset beside Firewall Reset. Restart your computer. As you use programs that access your network/internet, the firewall rules will be created again.

I reset the firewall and restarted both the PC and the iPhone.  The outcome was the same.  However, I noticed the first TCP packet arriving at the PC from the iPhone had the ECN and CWR bits set.  I understand this could be a problem with firewalls in the past.  Is it relevant here?

From above... 

In other testing, I discovered that a MacBook Air and an iPad both with Safari, and a PC with Edge could all connect to the Akrutosync server, but neither my iPhone nor my wife’s could.

What security software is on the PC with Edge?

Have you tried again on the affected PC? How did you disable the SmartFirewall and Auto Protect? From the right click of the Norton icon in the System tray?

Your diagnosis led you to feel it is a firewall issue. To reset the Norton firewall, from the main Norton Security screen click on Settings - Firewall. On the General tab, click on Reset beside Firewall Reset. Restart your computer. As you use programs that access your network/internet, the firewall rules will be created again.

 

 

peterweb:

My question about apps on the devices was meant to refer to any app for the Akrutosync feature. Is there an app required to perform the sync function? If so, maybe that needs to be tweaked for the latest update to iOS.

There are two phases.  The first phase uses Safari on the iPhone to communicate with the Akrutosync application on the PC over port 80.  In the second phase, an Exchange service is configured in the "Passwords and Accounts" settings on the iPhone.

In production, the Akrutosync application on the PC appears to the iPhone as an Exchange server.  Traffic is exchanged on ports 80 and 443.

There are no new apps on the iPhone.  I haven't been able to complete the first phase above if the Akrutosync application is running on a PC protected by NIS.  I am not aware of anything I can configure in the Safari settings that would account for the iPhone continuing to send SYN packets to the PC.

My question about apps on the devices was meant to refer to any app for the Akrutosync feature. Is there an app required to perform the sync function? If so, maybe that needs to be tweaked for the latest update to iOS.

 

 

Does the iPad also have iOS 12.1? Do both your phone and your wife's have 12.1?

My wife's iPhone, my iPhone, and the iPad all have 12.1 iOS.

You were able to complete the configuration. Does that mean you have the sync working correctly?

Yes, but it is based on my notebook which I would't normally use as often as the PC.  If I could, I would like to resolve an issue that appears to be NIS and iOS12.1 related

The timing of this sounds like it coincides with the release of iOS 12.1 on my iPhone. Maybe something in that???? Had you tried restarting your phones? Is there an app that gets installed on the iOS device? If so, did you try reinstalling that after the OS update?

I agree, the timing seems close to the installation of iOS 12.1 on my iPhone.  Unfortunately, I don't have an accurate memory of that and I haven't found anything yet relating to its changes that might be relevant.  I have tried restarting the iPhone and uninstalled two apps that were installed in previous weeks, even though the timing seems wrong.

In other testing, I discovered that a MacBook Air and an iPad both with Safari, and a PC with Edge could all connect to the Akrutosync server, but neither my iPhone nor my wife’s could.

Does the iPad also have iOS 12.1? Do both your phone and your wife's have 12.1?

To test this, I loaded Akrutosync on my Windows 10 notebook which uses Microsoft Defender rather than NIS and was able to complete the Akrutosync configuration flawlessly.

You were able to complete the configuration. Does that mean you have the sync working correctly?

This arrangement worked reliably until Tuesday 6 November about the middle of the day

The timing of this sounds like it coincides with the release of iOS 12.1 on my iPhone. Maybe something in that???? Had you tried restarting your phones? Is there an app that gets installed on the iOS device? If so, did you try reinstalling that after the OS update?