admin assist having issues with CEO's calendar syncing, Outlook, Exchange 2010

I have user that has full access to our CEOs email and calendar. She is a MAC and Windows device on her desk. Both are using Office 2016 products. She goes to one of her devices, lets say the Windows device and schedules a meeting in the CEO's calendar.
The meeting does not show up on the Mac or in his OWA calendar. This is a huge issue due to the people involved. I need all advice and trouble shooting suggestions possible. I am heading over to GOOGLE now to research on my own, but any input is welcome
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Thor2923Asked:
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RoninCommented:
You can start by providing Exchange version you have.
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Scott CSenior EngineerCommented:
@Ronin..Says in the title Outlook/Exchange 2016.  

The first thing I would try would be to try scheduling something using OWA.  And then look at the CEO's calendar using OWA.  The thing with OWA is that it is directly access the mail server.  There is no delay and no data can get lost along the way.

Make sure Exchange is running the latest CU.  When 2016 first came out it had quite a few bugs in it.
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Scott CSenior EngineerCommented:
BTW....is anybody else having this issue?
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RoninCommented:
Thank you Scott, I was asking for exact version.
e.g.
Get-ExchangeServer | fl *version*

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Thor2923Author Commented:
[PS] C:\Windows\system32>Get-ExchangeServer | fl *version*


AdminDisplayVersion : Version 14.3 (Build 123.4)
ExchangeVersion     : 0.1 (8.0.535.0)

AdminDisplayVersion : Version 14.3 (Build 123.4)
ExchangeVersion     : 0.1 (8.0.535.0)

AdminDisplayVersion : Version 14.3 (Build 123.4)
ExchangeVersion     : 0.1 (8.0.535.0)

AdminDisplayVersion : Version 14.3 (Build 123.4)
ExchangeVersion     : 0.1 (8.0.535.0)

AdminDisplayVersion : Version 14.3 (Build 123.4)
ExchangeVersion     : 0.1 (8.0.535.0)
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Thor2923Author Commented:
so what does that tell us?
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Thor2923Author Commented:
we made an appoint in OWA and no sync to other OUTLOOKS, we do not have direct access to the CEOs OWA, which makes it difficult since that is what we need to fix
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Thor2923Author Commented:
no one else seems to be having the same issue but no one has all her devices. Is there anyway to force a sync or settings somewhere we can check? Maybe we can tell outlook to check ever 5 minutes?
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Thor2923Author Commented:
are the deleted items the same as the dumpster? I have this info;
TotalDeletedItemSize    : 122.1 GB (131,086,268,054 bytes)      
RecoverableItemsQuota        : 250 GB (268,435,456,000 bytes)      
RecoverableItemsWarningQuota : 240 GB (257,698,037,760 bytes)      


should be plenty of room
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Thor2923Author Commented:
I am sorry our exchange is 2010 and outlook is 2016
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Scott CSenior EngineerCommented:
@Ronin....my apologies...I made an assumption and I was wrong.

What that tells us is that you are not running Exchange 2016 as stated in your question.

It also tells us that you are running Exchange 2010 SP3 with NO updates.

You are close to 4 years behind in your patches.

What happens if you use a different version of Outlook other than 2016?

You are using Outlook 2016 against a version of Exchange that is behind in updates.

You need to install RU17 for Exchange 2010.  https://www.microsoft.com/en-us/download/details.aspx?id=54934
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Thor2923Author Commented:
from what I remember the issue started after she received a new laptop with 2016 but we have server users on Outlook 2016. I am not sure if downgrading is an option. This is basically what is happening between the 3 platforms;

Windows      Mac       OWA
change         nothing         nothing
nothing         syncs              change
nothing         change              nothing
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Thor2923Author Commented:
sorry I wrote this question up with a little haste, I got the exchange version wrong
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Scott CSenior EngineerCommented:
Don't downgrade.  Install RU17.  See if that fixes the issue.
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RoninCommented:
The latest RU is 18, please install it.
However Exchange 2010 doesn't provide correct version in the PowerShell output.
Please run MMC -> HELP -> About.
Post screenshot.
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Scott CSenior EngineerCommented:
This command will get you the exact version of Exchange 2010.

Get-Command ExSetup | ForEach {$_.FileVersionInfo}
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Thor2923Author Commented:
ok Guys, I tried to move the CEOs mailbox to another mail database, just to see if I could, and it failed and gave me an error that the "dumpster was full" I GOOGLED some powershell commands and found he was set for 200GB for his Dumpster size, so I pushed him up to 350GB. I do not have access to all the devices in question but I did notice that there was VERY SLOW syncing between OWA and his actual mailbox in OUTLOOK. I was wondering if it was slow because he has such a HUGE mailbox and being the CEO, I cannot tell him to clean it up. Anyway, you guys have given me great ideas and input and got me looking at things I would not have thought of. I want to leave this question open for a little while incase the issue is not totally resolved. All I know is there was A problem and that was corrected, but considering the people involved I am not ready to declare victory yet
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Thor2923Author Commented:
issue appears to be resolved...thanks again
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