When I open a Markdown file into Lettera from the Finder, the Show/Hide Sidebar menu item is grayed out, nor is the sidebar button visible in the upper lefthand corner. It seems that I need to open the file from Lettera’s sidebar in order for the Show/Hide Sidebar menu item & button to be available.
I assume that’s not how things are supposed to work. I hope I’ve described the problem clearly.
Actually it’s obvious that no sidebar is displayed. After all you’re not opening a folder within Lettera but just a single file in the Finder. What folder would you expect to see in the sidebar after opening a single file?
It seems like he is anticipating being able to see the Finder location in the sidebar.
Yeah, sure. But what’s the exact location? Should the open file be displayed at the top level or rather the folder it is contained in? I think this strict separation works really well: Lettera as an app with a library/vault and as a viewer for individual files that are opened from other locations.
I think the OP is expecting the folder it is contained in. I’m in agreement with @krssno, that a separation makes the most sense.
If the Finder location was visible in the sidebar after opening a singular file, then you would also expect to also see all of the other folders and files within Finder on the sidebar. That would seem odd and cluttered.
Not to mention, if you had opened a singular file, presumably you did so from its location in Finder anyway.
I’m so much in favor of a strict separation that I wouldn’t even display a sidebar when individual files are opened from the file browser in their own window. At the very least they should open with the browser closed. But that’s actually a separate topic.
I’m not talking about a feature request, but an apparent bug. Hopefully these screenshots clarify:
When file is opened from within Lettera, using the Sidebar:
When the exact same file is opened from the Finder:
Shouldn’t Show Sidebar be available no matter where the file opens from? I should note that this file is in the Lettera iCloud folder.
It is greyed out because no sidebar exist.
If you open it from within the Lettera app, I assume you can see the sidebar. Right?
Yes, that’s correct. I guess I understand why it could make sense to disable the sidebar for some files, but I would think any files that are in the Lettera iCloud folder should always work with the sidebar regardless of whether I open them from the Lettera sidebar or from Finder.
Now I understand your confusion 
Good news: this is actually working as intended 
Let me explain the reasoning, because it’s a deliberate design decision driven by two things:
The first point is the important one. Lettera is distributed through the Mac App Store, which means it’s a sandboxed app: it can only access files you’ve explicitly given it permission to open (the one exception being Lettera’s iCloud folder, which we’re granted access to by default). So when you open a single file from Finder, that file is all we have access to, we can’t show the sidebar or its parent folder, because we simply don’t have permission to read them.
Your case is a bit special: the file lives inside the iCloud folder, so technically we could show the sidebar there. But then the app would behave differently depending on which file you double-click, and that’s confusing and hard to communicate. So we chose two clear, predictable modes instead:
Hope that clears it up! Let me know if anything’s still unclear.
There’s a special case - as I mentioned - when opening a file from Lettera’s file browser in its own window: the sidebar remains. I am not sure if I like it. On one side I was confused, on the other one it is a nifty feature.
What do you mean “folders that I have added”? Lettera has no concept of adding Folders, you can open a folder as a workspace, but folders with different roots can’t be viewed together.
The idea behind it is that you’ve started from a workspace and Lettera keep you there. Currently nothing is written into stone, we’re reading all the feedback and understanding how people want to use it 
When I open a file in its own window I usually do so just to view the content. At the same time however there’s no reason why the same workspace shouldn’t be displayed in more than one window. Keeping the sidebar closed when opening a file in its own window seems to me to be the best compromise.
Worth clarifying what’s actually happening there: dragging a folder into the sidebar copies it into the folder the current window represents; so iCloud Drive, unless you’ve opened a different folder as your workspace.
In other words, you’re not referencing your original folder in place; you’re creating a copy of it inside Lettera’s workspace. Referencing external folders without moving/copying them isn’t something Lettera does (the sandbox/security model is a big part of why). So those folders look persistent because they genuinely live in the workspace now, but they’re just no longer linked to the originals.
You’re right that this isn’t a sandbox limitation, it’s purely a design choice in how Lettera’s sidebar works.
In Lettera, the sidebar represents a single folder, 1:1. Because of that, dropping something into it can only mean one of two things: copy or move it into that folder. There’s no concept of “reference this folder but leave it where it is.”
iA Writer’s sidebar is built on a different model: it’s a generic space where you can reference folders and documents that live anywhere (likely via aliases under the hood, as you guessed). That makes iA Writer more of a shoebox app, whereas Lettera is a document-based app. The window is a folder, and what you see is exactly what’s on disk in that location.
Both are valid approaches; they’re just different philosophies. Ours keeps a strict, predictable mapping between the sidebar and a real folder on your drive.
You can pick any folder! And not just one, you can have as many as you want. Just open a folder via the “File → Open…” menu or drop a folder in the Lettera dock icon.
I like the way you’ve chosen to implement this. To make your choice more obvious, I would make it so that opening a single file does not open as a tab within the already opened Lettera window. Presently, when I open a single file, it opens as a second tab, which makes it appear to be living in the Lettera workspace. The only obvious way to know that it isn’t in the workspace is that the sidebar has disappeared.
