Office 365 Enterprise E5: the Plan, the Promise, the Process and the Pain

Jason Himmelstein

by Jason Himmelstein on 12/10/2015

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Article Details

Date Revised:

Applies to:
customer lockbox, Office 365 Add-Ons, Office 365 Enterprise E3, Office 365 Enterprise E5, troubleshooting Office 365 E3 to E5, upgrade Office 365 E3 to E5

I have been a long time Office 365 subscriber. In addition to using Office 365 for work at the companies I have worked for over the past five years, I have maintained a personal subscription for my own personal brand stuff. Being a Business Intelligence fan boy, the subscription that fit me best has always been the Office 365 Enterprise E3 at $20 per seat per month (PSPM).

That was until WPC this year when Microsoft announced the Office 365 Enterprise E5 SKU and I heard about all of the great new stuff that was coming in this new SKU. I’ve been paying $10 per month for PowerBI for Office 365, and when Microsoft announced that E5 will include PowerBI Pro AND PSTN Conferencing, I figured that it was going to be a winner from a price perspective.

On December 2, 2015, the E5 SKU became available to me in the Office 365 Admin cart. The price point was $35 PSPM. After a moment of consideration, the price point seemed, while not terrific, reasonable. Here is what tipped the scales for me:

  1. Included in the price is all that E3 = $20 PSPM
    1. Office Online & Office Pro Plus
    2. SharePoint Online
    3. Exchange Online
    4. Yammer
    5. Azure Rights Management
  2. PowerBI Pro = $10 PSPM
    1. Look at for details on the data refresh & collaboration features that do not come with the free version
  3. Skype for Business PSTN Conferencing = $4 PSPM and the rough equivalent to GoToMeeting, which starts at $24 PSPM
    1. Allows for attendees to join the meeting by dialing in using a landline or mobile phone as well as using PC and phone-based apps to connect and share screens
  4. Delve Analytics = $4 PSPM
    1. Insights to show you how your team communicates using Office 365. Set your own goals & measure your progress
  5. Customer Lockbox = $2 PSPM
  6. Office 365 Advanced eDiscovery, Exchange Online Advanced Threat Protection, Skype for Business Cloud PBX, & Office 365 Planner Preview = not features I know that I need yet for my small implementation, but are certainly of interest for larger enterprises

I figured that with all of the new features rolling out it would be worth the extra money to get Enterprise E5. I went into the Admin Center to switch my plan from E3 to E5 (figure 1), and when I did, the Admin Center said I was ineligible:

Office 365 E3 upgrade to E5 not automatic
Figure 1: Ineligbible to upgrade Office 365 Enterprise E3 to E5.

The link takes you to an article that suggests that you cannot switch plans due to Add-Ons. The article suggests that removing the Add-Ons will remedy the situation and allow you to switch plans. That sounded good in theory; however, when I attempted to set the Add-On quantity to zero since there was no remove button, I got the error shown in figure 2:

You get an error trying to remove Office 365 Add-Ons if you try to change the total licenses to 0.
Figure 2: When you try to remove Office 365 Add-On, you cannot set the total licenses to 0.

I decided to leverage Microsoft Support at this point since it didn’t appear as though I could do anything more to help myself. I used the Admin Center support mechanism and within a few minutes, a very helpful fellow named Ian called me back. We walked through everything that I had already done, as per protocol, and then he reached out to the next level support teams.

It turns out that the only way to “switch” from an E3 plan with Add-Ons to the new E5 plan is to purchase an E5 license, remove the E3 license & Add-Ons from the user, and apply the new E5 license to that user before saving.

Before and after: upgrading Office 365 Enterprise E3 to E5
Figure 3: To switch from E3 to E5, you must purchase the E5 license, remove the E3 license and Add-Ons from a user, and apply the new E5 license to the user before saving.

The issue with this is that now I have an E3 subscription that I am still being charged for that I no longer need. When attempting to cancel this subscription you encounter a cancellation fee. This is something that I am still working on with Microsoft at this point; however, I am up and running with my E5 license… or so it seems. When I close out and reopen my Office 365 browser session, Office 365 shows that it is still setting up things in the App Launcher (figure 4).

Office 365 Admin Launcher Setting Up after Upgrading to E5 SKU. This goes on for days.
Figure 4: After upgrading my E3 license to E5, Office 365 Admin App Launcher shows “setting up” for email and calendar and contacts.

My email is still flowing properly into Outlook 2016 and to my phone. However, I can no longer access any of the Exchange Online features through the App Launcher. Testing revealed that I could still access Outlook on the Web by visiting the URL directly when logged into Office 365, so I knew that my mailbox was intact & healthy. Knowing that things can take some time to provision, I decided that I should give it a bit and come back later. After all, I had just made the change… I shouldn’t expect things to provision and be ready that quickly, right? WRONG! Within 5 minutes of me applying the E5 license to my user account, I got my Skype for Business Dial-in Conferencing info (figure 5).

Office 365 E5 License Skype for Business Dial-in Conferencing set up quickly.
Figure 5: With an E5 license, Skype for Business Conference was configured quickly.

Blazingly fast setup experience! I was thrilled & impressed. Sadly, the App Launcher issue was not as quick to resolve…

After four days of the App Launcher still showing “Setting Up,” I decided it was time to open another support case. I looked at the user account in the Admin Center (figure 6) and found that it claimed to still be preparing the mailbox.

Office 365 E5 Admin Center preparing mailbox
Figure 6: Admin Center shows it is still preparing the mailbox.

This time the response from Microsoft Support was not quite as quick and I got bounced around to five different departments over the course of seven hours, each looking for the next team to pass me off to. When I got the email in figure 7, I had finally had enough and insisted on escalation.

Office 365 Microsoft Support too busy to help with my E3 to E5 license upgrade.
Figure 7: Microsoft Support is too busy.

After I sent a scathing email to the listed manager and underlying chain of command, the communication got much friendlier and faster.

The Exchange Online Support Team member, Amit, did his full load of troubleshooting and finally determined that the issue appeared to be Customer Lockbox. We went into the license and removed just the Customer Lockbox feature (figure 8) and applied the change.

Removing Customer Lockbox from Office 365 Enterprise E5 license
Figure 8: Removing Customer Lockbox from the Office 365 E5 license allowed the mailbox installation to complete.

Once this change was made, the mailbox “completed” it’s setup (figure 9) and all appeared right with the world again (figure 10).

Office 365 E5 license upgrade complete after Customer Lockbox disabled.
Figure 9: Mailbox installation complete.

Office 365 App Launcher E5 license upgrade is complete.
Figure 10: App Launcher shows that the apps it was setting up are complete.

While Customer Lockbox is not a feature that I am dying for yet, it is a part of what I am now paying for so I wanted to get it working. Amit and I went back into my user, added the feature back in, and then I logged back out and in again. My user returned to its previous state of “preparation,” however, my access to the Exchange Online features through the App Launcher remained.

At this point we have closed out the App Launcher case and there is an open case for the Customer Lockbox issue, which according to the case notes (figure 11), will be resolved on 12/13/2015:

Office 365 E5 upgrade Customer Lockbox support ticket
Figure 11: Microsoft is working on the Customer Lockbox bug for upgrading Office 365 E3 to E5 license.

With Customer Lockbox not being able to be provisioned at this time and the apparent lack of the Voice Features. no sign of Delve Analytics, or Planner… I am starting to feel a bit like I am eating the cookie dough before it’s put in the oven. I know it’s too early… but it sure can be tasty… and what’s life without a little risk, right? While I know the ultimate end game is going to be great, it is just a bit hard to swallow the high a price for something that isn’t fully baked yet…

Topic: Office 365

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