Lavi, that has never worked for me as-you-described since DungeonScrawl integration came out and I have tested/used this many times this past week-or-2.
There is a glitch in the process you described, it maybe bugged, alternatively (seems likely) it may just be a confusing GUI and unclear instructions.
In Roll20, Create New Page > Create New DungeonScrawl Map > it opens DungeonScrawl as a webpage with a Pop-Over that offers either Open Save File, or Create New > choose Click "Create New" in DungeonScrawl > Start drawing.
In Roll20 a blank page appears. Nothing you draw in DungeonScrawl appears in Roll20.
You have to get the Connect code from DS and then put it into Roll20, then it will show the drawing.
I am not on DS Pro now (I used to be). I'm not even signed-in to DS.
Note: the DS pop-over that offers only 2 choices "Open Save File" or "Create New" is persistent and loads as a Pop-Over every time you start a new DungeonScrawl whether you are Logged-out or Logged-in, whether you are DS Pro or Free. Please see SCREENSHOT 2 below.
Screenshots in 4 steps showing what I typed out the steps to describe, and the result:
My theory -- I think that users are expected to click away from the Pop-Over and exit-out of it to accomplish what Lavi is saying, but the pop-over itself does not offer that choice, and that would be a GUI problem if that's the hang-up here.
Step 1 in Roll20 click Create New DungeonScrawl,

Step 2, DungeonScrawl opens and the only 2 choices are "Open Save File" or "Create New" so choose Create New: (NOTE: If the instructions is not to press Create New then please make this more obvious, because please look at the screenshot and playtest this workflow again and you'll see this):

Step 3 now you have a blank DungonScrawl that you can draw on:

Step 4 go back to Roll20 Tab and your drawing is not there, because the DS is not Connected yet:

The End.
It seems like Roll20 wants people to Exit-Out of the DS Pop-Over screen, but there is no indication to do this. It's not mentioned in the instructions that has been posted, but more-importantly it's not mentioned in the GUI (the interface).
Thanks for your consideration of this issue.
Lavi said:
There seems to be a bit of confusion here. Pressing "Create New dungeon Scrawl Map" should automatically open up a Dungeon Scrawl tab and also create the connection without any additional steps. The Help Center had a quick 1-minute video to showcase this, that many users have found helpful.
There may be some additional variation here if, for example, Dungeon Scrawl Pro users are taking steps to sign in and are pulling up their auto-saved maps from their Dungeon Scrawl library. This is where specific steps being taken would be really helpful to nail down the confusion.
Gold said:
iuzbob said:
Since yesterday it is no longer working for me. I tried Chrome, Edge and Firefox. I create a new page via the drop down menu and start drawing in Dungeon Scrawl. But there is no update on the roll20 page. Anything amiss here?
Reading this closely, you actually didn't say the proper steps. You created a new DungeonScrawl page from the drop down menu. Then comes the part you didn't mention. You need to go on the Roll20 icon in the Dungeonscrawl and copy the Connect code, and go to the Roll20 Pages and use the dropdown and choose Connect Existing DS page.
I think maybe that's what's confusing about the Create new DungeonScrawl button in Roll20. It creates but it isn't connected, until you use the other button in the dropdown that says Connect Existing.