After an amazing week in Wigtown, walking and running all over the place, I was looking forward to analysing City Strides to see how many new streets I’d ticked off.
None. That’s how many new streets I ticked off. We had walked or ran in Newton Stewart, Whithorn, Portpatrick, Stranraer and of course most of Wigtown.
I zoomed in on the website and examined every town. Nothing. I followed the forum to a link which contained a spreadsheet for missing cities. There were dozens of missing towns in Scotland.
City Strides is a great Strava add on, and is the work of just one person. Hopefully, at some point in the future this beautiful area of Scotland will be recognised by City Strides.
Beards and Triathlons 
I had a similar issue with Wales in the past. It all comes to what defines an area in OpenStreetMap and apparently the level was different for Wales vs England so maybe same here? This was my post on the forum at the time https://community.citystrides.com/t/talking-about-australia/22881/18?u=m_l_heywood