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Updated: Mar 11, 2021

We have had Teams in our company for 2 years! In the dreaded Islands mode (cue the scary music). If you know anything about hybrid environments, you will know this is not ideal. Unfortunately, these decisions were made without my input, with no plan and a "here you go, have fun, good luck!" attitude.

Well, times are changing! One thing to thank Covid for (if that is appropriate). Our company realizing Teams needed training, a strategy and a migration plan.

This is where our Team comes in...Migration!

PLAN -> Design - > Deploy


Step One: Ensure your Hybrid environment is configured

Step Two: Get out of Islands mode - FAIL

You should do this! It will help your end users be less confused on what to use Skype for and what to use Teams for.

Set the Coexistence mode.

  • Islands - Use this setting if you want users to be able to use both Skype for Business and Teams simultaneously.

  • Skype for Business only - Use this setting if you want your users to only use Skype for Business.

  • Skype for Business with Teams collaboration - Use this setting if you want your users to use Skype for Business in addition to using Teams for group collaboration (channels).

  • Skype for Business with Teams collaboration and meetings - Use this setting if you want your users to use Skype for Business in addition to using Teams for group collaboration (channels) and Teams meetings.

  • Teams only - Use this setting if you want your users to use only Teams. Note that even with this setting, users can still join meetings hosted in Skype for Business.

The problem with this design is if you go to SfB w/ Teams Collab, you lose the ability to create meetings and chat with users. You get the meetings function back with Collab and Meetings, but you still can't chat.

Personally, I think this is a poor design. Skype's most used function is chat...why wait until last to have users move to it?! Because remember, you are supposed to get out of Islands most ASAP. *sigh*

Step three: How are you going to use Teams?

Get these guidelines set before deploying! Set user experience and expectation right from the start.

Work with your business. Listen to what users are asking for. It is easier to GIVE additional capabilities, rather than take them away. Basically, if you're unsure if you should give your users permissions to do it. DON'T. Wait. Review the need after deployment.

Step four: Prepare your Network!

Use Network Planner

This will help you determine your network requirements

Make sure UDP ports 3478-3481 for all locations.

DNS needed for Skype federation:

CNAME -> sip->2600->

CNAME -> lyncdiscover->3600->

Use the Call Quality Dashboard to understand the quality of calls and meetings.

Step five: Prepare trainings for your users - DON'T SKIP THIS STEP

Microsoft has great information to help your users learn Teams.

Take some time to put information together. Let your users know how you expect them to use Teams and how. This is so important for adoptions and morale!

Go to my next blog post Skype for Business On-premises -> Teams ->DESIGN Stage

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  • Writer's picturesamanthaeasterday

Updated: Apr 6, 2021

UPDATE: Passed!

For years I have been wanting to be officially certified in something Microsoft. My company does not cover those costs, so out of pocket, here I go!

I've never studied for an exam like this, not exactly sure where to start, but start I must.

MS-700 Managing Microsoft Teams, I'm coming for you!

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  • Writer's picturesamanthaeasterday

Updated: Jul 7, 2021

After a year of working from home, making changes to our network, security, infrastructure, our UC Skype phones decided to not let a different user sign into them.

We would receive this error when trying to sign in:

Well, what changed caused this?? Only the Skype Gods know....


Current, logged in phones work. You can log out of a current logged in phone and log it back in with the same extension. But you cannot log it in with a different extension.

What I have done so far:

Read everything by the infamous Jeff Schertz. He's seriously amazing and documents how to troubleshoot UC Phones extensively. This blog was very helpful

One of the first steps to do when you start troubleshooting is to run Test-CSPhoneBootstrap. Unfortunately, (I don't say this often) there were no errors. This one time, I wanted an error. Something to go off of at least.

One change, that is always worrisome....certificates. I did update the Skype Server certificate earlier this year. I had hoped that was my issue! But everything seems to be set up correct. I can see the phones are getting the correct certificate.

Next step, logs...

I started with Polycom phone logs. These logs are meant for Polycom support technicians, but I had zero luck getting any help from them to understand what was going on. So it was up to me! Luckily, Jack Stromberg showed me the way .

After a week of going through logs and logs and logs, researching every error, I was lead down the rabbit hole of DHCP.

Unfortunately....yet again....our DHCP options were correct. Again, another instance where I just need something to go off of.

And nothing against my love of Skype for Business, but the logs for phones on the servers, were very little, to no help.

One change that was done, right before the pandemic, was a firmware update on the phones. I followed the correct process though! Tested the update on 2 phones, logged in and out with different extensions, waited a week before pushing the update to all the phones. Everything seemed to have gone well! Then...we didn't enter our buildings, change phones, add phones for almost a year.

After a lot of time and energy on this issue. We finally figured out it was a tls 1.0 issue. By using a different Poly brand phone that supports tls 1.2. Microsoft did depreciate 1.0 support. But I could not figure out, where in our company, this had been disabled. Truth is, we never did find out where it is getting blocked. Which is a problem for moving to TeamsOnly using the Admin center as well (search for related blog post). But this issue turned out to be a blessing in disguise! I started to question the need for physical phones anymore. With enterprise voice, we carry our phones on our laptops, why not just plug in a usb, Teams/Skype support external speaker, join your meeting on your laptop and be done! So that is where we are going! It's always good to question what is 'usual' or 'normal' and ask why?

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