To add to the list of items of issues I have with Office 365 😊

-          Third party application support. What protocol does your internal 
applications require? If its just SMTP or mailbox access via POP3 / IMAP4 then 
you are fine. If it is MAPI access then you will most likely face challenges

-          DL migration to Office 365. Since a distribution group is simply a 
AD (universal / security) group object migration is not an option. You will 
essentially have to recreate those DL in Office 365. There are a few scripts 
for them but it’s a pain

-          Public folder migration if you have them (this really goes for any 
environment if going from traditional PF to Modern PF, I would personally say 
do Remove-PublicFolder -Identity \ -Recurse -Confirm:$FALSE but I don’t think 
anyone wants to get fired)

-          eDiscovery searches are limited in size (from experience and a past 
premier case we opened a few weeks ago) and will simply fail if the search 
context is too large with no real warning.

-          Service outages are something you do not control. Example, the IMAP4 
outage recently that went for about a week. We had to migrate application 
mailboxes back to the on premise environment so those third party applications 
worked

-          EOP configuration. EOP out of the box is a bit generic and does not 
do an “excellent” job at blocking spam (compared to other third party vendors) 
but at the same time you can setup a few ETR to combat that issue (EOP does 
have some nice things like inbound DMARC check, which can be applied in a ETR 
if inbound DMARC fails)

-          Delegate mailboxes during the migration phase. So if you have a user 
on premise that has to access someone’s mailbox in Office 365 (full access, 
send as) it doesn’t work. It does work (full access permissions) if the mailbox 
the user is accessing is on premise and the user is in Office 365, but Send As 
/ Send on Behalf Of permissions do not. I think this has to do with the way the 
attributes for those properties are kept, and DirSync cannot replicate them (I 
think they are protected attributes). So if you are not doing a cutover 
migration, and doing a long term hybrid then you need to plan appropriately. I 
honestly didn’t know this at first when I did my first migration years ago and 
the CEO’s assistant wasn’t that pleased with me.

-          Managing distribution groups. I think this was fixed in Azure AD 
Connect but the “ManagedBy” attribute is not synced to Office 365 / Azure AD. 
This means that if you want to manage a distribution group in Office 365, and 
that distribution group is still on premise you will need to use AD tools to do 
so (https://support.microsoft.com/en-us/kb/2417592)

-          Troubleshooting methods are a bit more difficult than on premise. 
Want to pull CRA logs? Only the Get-CalendarDiagnosticLog works and the actual 
analyze command (which works for 2013+) does not. There is no event viewer, and 
you cannot see the IIS / RCA logs anymore. To me that is a huge negative since 
I am now bound to whatever troubleshooting I can do at the client level along 
with whatever PowerShell options are available in EXO.


Sent from Mail<https://go.microsoft.com/fwlink/?LinkId=550986> for Windows 10

From: Michael B. Smith<mailto:[email protected]>
Sent: Thursday, February 18, 2016 12:22 AM
To: [email protected]<mailto:[email protected]>
Subject: [Exchange] RE: Upgrade on-prem vs Office 365

#4 is a major ongoing PITA.

Especially since it is now extremely difficult to control when updates are 
applied to Office and to know "who has what" update. Also, the status windows 
don't tend to be updated until hours after an event begins, and will only be 
updated if a 'significant' percentage of Office 365 users are experiencing a 
problem.

From: [email protected] [mailto:[email protected]] On 
Behalf Of Michael Tavares
Sent: Wednesday, February 17, 2016 7:03 PM
To: [email protected]
Subject: [Exchange] RE: Upgrade on-prem vs Office 365

Cached exchange mode won't help much with #1.  The email is still being 
downloaded from the server and using bandwidth when it happens. Generally not a 
big deal if the email doesn't contain file attachments.  If you happen to be a 
company like my previous company that got 10's of thousands of very large 
attachments daily, then it becomes a very big issue.

The other issue with exchange being in cached mode, is the users that have 
large mailboxes and the cache runs their C: drive out of space.  (not many 
companies I know of that install office on a drive other than C: ).  Yeah I 
know with newer versions of outlook you can limited how much gets downloaded in 
the cache.  That sometimes helps but not always, depends on the user.


From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]] On Behalf Of Freddy Grande
Sent: Wednesday, February 17, 2016 2:02 AM
To: [email protected]<mailto:[email protected]>
Subject: [Exchange] RE: Upgrade on-prem vs Office 365

As long as you're using Cached Exchange mode on your Outlook clients 1 and 4 
and as huge an issue as they sound.
One thing I suggest while you train you users (oh yes, you'll want to train 
them with regards to Archive Mailboxes, retention policies, Junk Email (if not 
already handled by O365) remind them to dial back on attachments, especially to 
groups or many recipients where possible.

We've been trying to push OneDrive for Business for internal sharing of 
folders/documents and our FTP server for external bulk documents to share with 
other companies.

Regards,
Freddy

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]] On Behalf Of Michael Tavares
Sent: Wednesday, 17 February 2016 10:25 AM
To: [email protected]<mailto:[email protected]>
Subject: [Exchange] RE: Upgrade on-prem vs Office 365

I can give you my 2 cents.  We migrated a few thousand users a couple of years 
ago.


1.        You will probably need more internet bandwidth.  This will really 
depend on a few things,  how heavily used is your internet connection 
currently, number of users, and how many file attachments users are going to be 
opening daily (and of course the bigger the size limit the more bandwidth they 
will consume)

2.       Be prepared for some users to not work, and others to work.  Since 
your mailboxes get spread out across servers it is possible for 1 or more users 
to have issues while other work fine.  This was always annoying as the outages 
at MS always seemed to find my C-Level execs mailboxes, very rarely just a 
regular end user

3.       Backups in general.  I had several issues were a users mailbox became 
corrupt and after several days of dealing with premier support the 
determination was made the mailbox and it lagged copies were corrupt and the 
only option was to delete the mailbox and recreate it (not an option when it is 
an execs mailbox).  So make sure you have someway to back up your mailboxes.

4.       I have been away from the day to day management of o365 for a little 
under a year, but Regular support when I left was HORRIBLE.  And while Premier 
support was not much better, it is something to keep in mind when making the 
decision.

5.       While #1 will have some to do with this,  your users need to remember 
their mailboxes are in the cloud.  As a result, that nice speedy 100/Full, or 
GiG/Full connection they had to your local network which allowed them to open 
file attachments quickly, has been reduced significantly by the your internet 
connection and distance to o365.  So file attachment that would take 1 or 2 
seconds to open, probably now result in outlook displaying the good old, 
outlook not responding as it opens/saves the attachment.



From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]] On Behalf Of Damien Solodow
Sent: Monday, February 15, 2016 9:46 PM
To: [email protected]<mailto:[email protected]>
Subject: [Exchange] Upgrade on-prem vs Office 365

Our on-prem setup is Exchange 2010 SP3, so we're going to want to look at a 
migration of some variety later this year.

We already have an Exchange hybrid setup with Office 365, and are considering 
just migrating our mail to there rather than an on-premise upgrade.

What are some of the negatives/issues/things we'd lose going cloud vs on-prem?
Main things I can think of are:
-likely need more Internet bandwidth
-won't have archival backups of stores/mailboxes
-?

DAMIEN SOLODOW
Senior Systems Engineer
317.447.6033 (office)
317.447.6014 (fax)
HARRISON COLLEGE


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