It could be web sockets, this could show you what I mean:

https://asana.com/guide/help/faq/connectivity#gl-websockets

You have to white-list some stuff sometimes to get it to work
correctly, but I think that is what I was intercepting vs inspecting.
This was an example white list I had for skype and asana:

asana.com sling.is apps.skypeassets.com login.skype.com pipe.skype.com
secure.skype.com config.skype.com api.skype.com ui.skype.com
s.gateway.messenger.live.com get.skype.com dsn13.d.skype.net
mobile.pipe.aria.microsoft.com a.config.skype.com www.skypeassets.com
dr.skype.net apps.skype.com api.asm.skype.com sync.app.asana.com

Try white-listing problem sites.

On Thu, Jan 11, 2018 at 10:30 AM, Roberto Carna
<[email protected]> wrote:
> Dear, I've created a self signed CA Certificate in pfSEnse, in order
> to use it in the SSL Filtering / Spice All from Squid.
>
> This CA certificate is NOT installed in none of the device clients
> (notebooks, cell phones, etc), because is imposible to ask each WiFi
> user to install it.
>
> Everything works OK, except certains cases, for example:
>
> - Facebook app sometimes doesn't load the user profiles, I have to
> close Facebook and open it again
> - Mercadolibre is the same, it doesn't load the content and after that
> I have to close and open the app
>
> Why certain apps don't work OK until I close and restart them ???
>
> Thanks a lot again!!!
>
>
>
> 2018-01-10 3:51 GMT-03:00 WebDawg <[email protected]>:
>> Can you just do inspection on this and have it stop acting as a true proxy?
>>
>> Splice All:
>> This configuration is suitable if you want to use the SquidGuard
>> package for web filtering.
>> All destinations will be spliced. SquidGuard can do its job of denying
>> or allowing destinations according its rules, as it does with HTTP.
>> You do not need to install the CA certificate configured below on clients.
>> Content filtering (such as Antivirus) will not be available for SSL sites.
>>
>> On Tue, Jan 2, 2018 at 11:01 AM, Elijah Savage <[email protected]> 
>> wrote:
>>> Interested in what sort of problems you are seeing.
>>>
>>> I use the same setup in a small environment let's call it home :) with many
>>> different devices and have not seen any issues.
>>>
>>> -----Original Message-----
>>> From: List [mailto:[email protected]] On Behalf Of Rainer
>>> Duffner
>>> Sent: Tuesday, January 02, 2018 10:01 AM
>>> To: pfSense Support and Discussion Mailing List <[email protected]>
>>> Subject: Re: [pfSense] Transparent proxy for WiFi users
>>>
>>>
>>>
>>>> Am 02.01.2018 um 14:46 schrieb Roberto Carna <[email protected]>:
>>>>
>>>> Dear, I've setup a Squid transparent proxy + Squidgard on pfSEnse 2.4
>>>> in order to filter HTTP and HTTPS web content for different types of
>>>> WiFi clients on my company:
>>>>
>>>> - Android (different versions)
>>>> - Notebooks Windows 7/10
>>>> - Iphone
>>>> - Etc.
>>>>
>>>> In some cases, depending on the device Operating System, some apps
>>>> experiment problems, for example Facebook and some others.
>>>>
>>>
>>>
>>>
>>>
>>> Apps that do hardwired Key-Pinning (everything from Apple, Google and
>>> probably TFB, too) will not work.
>>> You have to make exemptions, AFAIK.
>>>
>>> Same for ebanking and related.
>>>
>>>
>>>
>>>
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