Jump to certain folder in save as dialog

Try command option L to open the downloads folder. also consider updating so he can use a newer operating system with more security fixes. Maybe turn on keyboard hints. It might make him insane but at least he can maybe see where he's going off track.

Alternatively put you in list mode cmd-2, vo follows easily.

Isn't there something like voice over follows curosr or something? I don't understand how it works but perhaps, if you have the old mac, go through every setting and figure out how he had it, then try it on the new one. Others can help better then I.

No, this is effectively an active bug stil present on Sequoia unfortunately.

If the user needs the same folder repeatedly, they can add it to the sidebar. Customize the sidebar on Mac.

I've essentially given up attempting to organize my own data. Anything coming into my computer, from whatever source, goes in Downloads, and that has become my work folder for all current project. Believe me, it's quite a mess. I find what I need with first-letter nav (which seems to work fine for me in any Folder window). I avoid the Finder find utility like the plague. It simply doesn't work, as near as I can tell, though my sighted friends swear by it. Where was I? Oh. When I'm done with a project, I move files and folders from Downloads and into some appropriate subfolder of Documents, where I almost never reference them again.

Rant follows.

Back in my mainframe, Unix, and DOS days, selecting a save location was something I did routinely. The filesystem was designed to work like a filing cabinet. You organized it the way you wanted, and stored files where they made sense to you.

Then, at some point, Microsoft released a new version of Windows that made it very easy to save files in a folder called MyDocuments, but quite challenging to save it anywhere else. This was done, apparently, because Windows had attracted a lot of computer illiterates who didn't know how to organize their filesystem, and they could never remember where they stored their files. I don't believe MyDocuments improved the situation. At least initially, I had no idea where the "MyDocuments" folder was located.

Tragically, this UI pattern has expanded and bloated. We now have designated folders for Pictures, Downloads, Music, and inumerable other things, more or less forced upon us by the default behavior of not just Microsoft but also Mac and Linux. The pattern has its fingers everywhere. For example, we already have a filesystem that lets you sort and organize your files. But because MacOS assumes you'll store all photos in the Photos folder, they felt compelled to add an additional redundant organizational UI to the Photos app. Instead of providing a solid interface for the filesystem, manufacturers and app designers all create their own ad hoc and non-standard interface for organizing app-specific content, and the result is an explosion of interfaces we must learn, all of which do essentially the same thing.

My advice: develop a system that is as simple as possible, as elaborate filesystem organizations have become a thing of the past.

Possibly related: Keyboard focus synchronization is broke.

Here are four suggestions that might help. One, if VoiceOver tells you focus is in a scroll area,, try interacting (VO+Shift+down arrow), then navigate to find the List View. Once you do, first-letter nav should work. Two, escape out of the save dialog and try to save the download again. Three, Command+F5 toggle VoiceOver off and back on. Four, find the save dialog current folder pop up and change it to the parent. These are all things that seem to work around this issue for me.

What about syncing your VoiceOver cursor with your keyboard cursor? I don't remember what the hotkey is, but there is a hotkey to do this on Mac. So that way, when you do single letter navigation to get to a folder, press whatever the hot key is to sync the VO cursor with the keyboard curser, and you should be good to go.
It's an extra step, but better than nothing.

Nah it doesn't work there.

Something that works for me is to press command tab, and press command tab again to get back to the save as dialogue. I sometimes have this issue in finder, and pressing command tab twice like this does the trick.
Don’t hold command while you press tab twice, because that would go to a different app probably.
Press command tab, let it open the other app, then press command tab again to get back to the application with the save as dialogue. You might need to do this once or twice in order for first letter navigation to work.
On a sidenote, using control option F in a finder window or in a save as dialogue does not work, and causes things to start not responding.
In a world where NVDA or Jaws is on the Mac, opening the fine dialogue would probably not cause this issue. But sadly, we do not live in such a world.

Yeah, tell me again why macOS is so much more amazing than any other operating system?

Could someone experiencing it document the exact steps to reproduce this issue and send the report to Apple? I'll report it if I can reproduce it.

You can type Command-Shift-G and specify the entire path; ~ standards for home directory, as usual in UNIX. In fact, you can specify the entire path and file name in the dialogue opened with Command-Shift-G.

If you can get first letter navigation to work in Finder, you could press command option C on the folder/file you wanted, open the dialogue, press command V, and hit enter to be taken to the folder/file.