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Outlook won’t connect to Office 365 account


It seems like a very common situation: user has an account in office 365, wants use Outlook, tries to add Office 365 email account. Result is that they are faced with:

  1. A prompt for AzureAD credentials.
  2. A slow “Adding your account…” screen, which inevitably results in…
  3. A very unhelpful error message: “Something went wrong and Outlook couldn’t set up your account. Please try again. If the problem continues, contact your administrator”

After lots of searching the web, I didn’t easily find the cause. This was a problem I wasn’t sure whether to put down to a number of recent changes. IT could have been due to:

  1. Turning on Multi FActor Authentication (MFA) for the account in question
  2. Connecting to the account from a newly Azure AD (AAD) joined device
  3. Using Intune for the first time to deploy Office 365 to the machine in question


Feel free to skip straight to the solution, but this section gives some more context in which the error occurred and may be useful to see whether it is the same as your situation.

In the end I realised, that when it was prompting for the Azure AD credentials, it was wanting an App Password, which I had forgotten was a thing, and had been supplying it with the user’s credentials.

“But…”, I said to myself, “surely in 2020 we are not expecting Outlook 2019/365 to be using an App Password, that is supposed to be for legacy apps…..”. Correct, but ignoring that Outlook is a piece of crap and should have had its day a decade ago… it does actually support “Modern Authentication”, otherwise known to the rest of the non-Microsoft world as OAuth2, but it relies on having a setting set in Exchange Online to enable that functionality. According to Microsoft documentation, this was turned off by default for any domain that was using Office 365 before 1st August 2017.


You need to enable OAuth2, aka Modern Authentication, to prevent the prompt for a password when connecting to Office 365 on an Azure AD joined device.

You might be hoping that you could just go in to the Exchange Admin Center and check a box to enable it… Wrong! No, you have to download a Powershell cmdlet to do it. Before you attempt to do this in your favourite browser, STOP! It has to be IE11 or the brand new (Jan 2020) Chromium-based version of Edge which support “click once”, whatever that is.

You will need to run the command to enable OAuth2 as an administrator in the tenant that you own. Depending on whether that account has MFA enabled, you need to follow different instructions. The Microsoft documentation explains the process, but I will summarise below.

Log in to the Exchange Admin Center

For non-MFA accounts, click the first configure button. For MFA-enabled accounts, use the other configure button that makes reference to this. The instructions below use an MFA-enabled account.

It should download and install some remote powershell cmdlets.

Run the following command in a cmd prompt:

if you get an error, open Windows Services on your PC and make sure that “Windows Remote Management” service is running. It wasn’t for me. After starting it, and re-running that command I received the necessary “Basic = true” confirmation.

Go back to the powershell prompt and run the following to connect to your domain, replacing the UPN with your admin account obviously. It should popup a box asking for any MFA details needed:

Then run the following command to check whether Oauth2 is enabled or not. If you were getting the error at the top of this post, it should show as disabled.

Run this command to enable OAuth2 in exchange:

You should now be able to connect Outlook successfully. If for any reason you need to disable OAuth2 again, you can run this to disable it:


Things to do around the Forest of Dean with young children

If you are anything like us, you end up endlessly researching before holidays to find age-appropriate things to do, so here are some ideas based on our week away in case anyone goes googling “things to do in the forest of dean with toddlers”!!

We stayed at Whitemead Forest Park in the Forest of Dean. The village was called Parkend, and all the things we did were no more than a 45 min drive from there. We have a 3 year old and a 6 year old, and both managed/enjoyed all of these things, so we consider it a successful holiday! We visited in the summer holidays, and the weather was dry, which may mean some of these things are not as nice to do at other times of year.

General tips:

  1. Make more of your day out by visiting when there is something extra going on. See Raglan castle and Heritage Centre below
  2. Have an OS map of the area and keep it in the car. Get a rough idea of the route you’ll be going, and DON’T TRUST Google Maps, which tried to do some very peculiar things. If you start seeing moss growing in the middle of the road when following a satnav, it is likely taking you the wrong way!

Day 1 – Explore the forest

Visit Beechenhurst. This is one of the larger Forestry Commission sites, and has a large well-equipped visitor centre with cafe, play area, shop etc. At the time of writing this was running a Zog trail (pay a couple of pounds for an activity bag that involves finding clues hidden along a trail) although I suspect this will vary from time-to-time with whichever is the current trending Julia Donaldson story!

What wasn’t especially apparent was that your ticket price also includes parking at other nearby Forestry Commission sites during the same day – Symmonds Yat Rock, Cannop Ponds, and Mallard Pike lake. So plan to make the most of your ticket price.

As we only found this out later in the day, we only had time to visit one of these – Cannop Ponds (which is on the way back to Whitemead if you are staying there). This was a very nice spot, with streams to paddle in, and an easy and not-too long circular route around a lake, even for the 3 year old on a balance bike. It was so nice, that we made a second visit here before the end of the holiday.




Day 2 – Explore a castle

There are apparently over 600 castles in Wales. Many are real ruins – not that exciting, but there are lots more intact ones. We visited Raglan castle, partly because it was better value entry price than a lot of others (£21 for a family ticket) . It has an unusual layout with the Keep separated from the rest of the castle by a bridge crossing a moat within the caste walls. A tall tower to climb up and see the surrounding Welsh countryside. The castle by itself would have been worth a visit, but you would maybe have only spent a couple of hours there. We planned to go on a day when there was a Bird of Prey demonstration. This was a fantastic setting for the event, I have to say, and really made it into a full day out. I would highly recommend this strategy of choosing to visit places when they have a special even on – it makes so much more of the entry cost, and fills the day better.

Day 3 – Risk a proper walk

You were keen walkers before you had kids and pine for those days once more? It might be worth trying it! We have risked this a couple of times, and so far it turned out ok!

This time we selected Skirrid Fawr (aka Ysgyryd Fawr) – more of a hill than a mountain, but something that would nevertheless feel like an achievement. I am pleased to say that both children managed this – 6 year old skipped along it quite easily, 3 year old felt like they were (and actually were) pushing the boundaries, but both motivated well enough by a few snacks.

You park at a National Trust owned car park at the bottom (£3 for non-members). Ascend through a wooded area. Pass through a gate, and turn right. Soon you reach another junction. You can go left, going clockwise around the base of the hill, and then you will have a short but pretty steep ascent to the summit. With this age child, I wouldn’t recommend that. What we did was ambitious enough, which was to turn right, and go up a long, gradual incline along the ridge to the top, and then came back the same way. Lovely views all around.

Don’t be tempted to tell them they’re near the top too soon as there a couple of false summits before you actually reach the real one. Only announce it once you can see the trig point, as it’s quit a long (but flattish) walk.

On the way back, we stopped off at a National Trust oddity called The Kymin, which is up the top of a hill, overlooking Monmouth. Can’t spend any length of time there, but another nice view. Free to park, even for non-members.

Day 4 – Butterfly zoo, mini golf and hedge maze

These three attractionas are on the same site and known collectively as The Wye Valley Visitor centre. Wasn’t quite sure what to expect – variable reviews online and websites are somewhat “special”. However, we managed to spend a decent half day or so there between the three things. Butteryfly zoo is smallish but still plenty of interest. We didn’t spend too long in there as the kids were freaking out. Golf and hedge were good enough fun though. They had chunky child-size putters for little ones. Big outdoor and indoor picnic areas.

Book online in advance (i.e. up to the day before) is the best way to get the cheaper tickets, as you can then get the golf at half price. We paid online the day before so we knew the weather would be ok, and took advantage of the 50% off offer on mini golf.

!Parking! – plenty of warnings about this online, but as long as you go by the book, it is ok. Best thing to do is pay at the end so that you know how long you’ve spent there (most complaints are by people who paid on arrival and then went over the allotted time). Once paid, go in to the visitor centre and get your £2 parking rebate.

Explore King Arthur’s Cave and Symonds Yat Rock

This was done after visiting the butterfly zoo etc, as it was nearby.

This is a cave in a limestone cliff. There is a car parking lay-by for about 4-5 cars at the top of a very obvious path that leads downhill. Being a fairly high profile cave (well, it’s marked on tourist maps anyway), I was worried that it would be too busy to get parked, but actually we didn’t see anybody during the half hour or so that we were there, and there were no other cars. If it is full though, there is a car park (which may need paying for, we didn’t need to find out) at the Little Doward camp site, just around the bend.

Set off down the path – it’s not very steep – you see various bit of its abandoned past as a quarry, and eventually it opens up and you can see the limestone cliffs. At this point there is a fork in the path, and you want to keep right to go down the hill with the fields on your right. You start to see a couple of small caves/crevices, and can see trees growing directly out of the limestone face which is quite cool. Eventually you reach the bottom of the hill and it opens out to a clearing where you can enter the main cave. Take your torch/phone in and look up to see scary spiders dangling above your head! It’s amazing to think that various tools from ancient man have been found there, as well as wooly mammoth bones!

We just went back up to the car at this point, but if you are wanting a longer walk you can carry on a few different paths to see the “seven sisters” rocks and others.

Info board near car park

You’re also in the vicinity of Symonds Yat Rock, so might as well go there to take your photo of this iconic view. This is Symonds Yat East, which has a large car park, cafe etc.

Day 5 – Find out about the forest

We visited the Dean Heritage Centre. This offered a fascinating insight into the history of the forest, of which there was a lot more than I was aware, e.g. the tradition of free mining.

There were lots of historical artifacts, from ancient times up to present day, and for children lots of interactive things like dressing up, brass rubbings, “smells of the forest”, microscopes to examine things from outside. There were manned craft activities available although I don’t know if these are always on. This was another place we visited on a specific day after noting that they were running special events about “how to live in the forest like our ancestors”. There was an area set up for learning about celtic/anglo saxon trades – how to make bread or a mud round house, soldier training for children, all very interactive. We also joined a guided walk in the woods learning about survival techniques, what to look out for, firemaking.

It wasn’t very busy, which I was a bit surprised about as there aren’t too many things like it in the area. I thought that was a bit of a shame as they had tried really hard! We had a really good full day out there because of these extra activities, so look out for something that’s on during your stay!