Opening old .cwk files

Rather than using the "open with…" method, open LibreOffice & then drag the .cwk file to the LibreOffice icon in the dock or the "recent documents" window in LibreOffice. You may have more success opening one file at a time although I was just now able to drag 5 .cwk documents to the recent documents window of LibreOffice & they opened. These were a variety of types of AppleWorks documents - draw, paint, DB, word processing & spreadsheet. LibreOffice did freeze when closing two different DB documents. A lot may depend on the version of ClarisWorks or AppleWorks that last saved the document. I can tell that one of those documents was last saved with AppleWorks 5 by its modified date. The others were last saved with AppleWorks 6. I don't have any older files to try.

This experimentation was done with LibreOffice 7.2.5.2 on macOS Mojave. Version 7.2.6 is the latest stable version of LibreOffice.

At what point did LibreOffice quit? Opening a particular file or all files? Closing a file? Trying to save a file in another format, i.e. Word, Excel, ODT, etc.? Copy & pasting content into something else?

I would try opening only a few documents at a time. Better yet, one at a time. And then save the documents in another format as soon as you have opened them. I wouldn't even try copying & pasting content into anything else until it has been saved as something more modern. LibreOffice gives you lots of options. At a minimum, if the files open, you could take a screenshot to see the content. It depends on how valuable the data is to you as to how much effort you want to put into recovering these files.

When you realize that AppleWorks was declared end-of-life in 2006 or so & the last OS that was able to run AppleWorks 6 was Snow Leopard (Mac OS X 10.6.8) it is amazing that it is at all possible to open its files with any kind of accuracy on a much newer macOS. AppleWorks/ClarisWorks 5 & earlier require classic Mac operating systems. I find that LibreOffice retains the formatting of AppleWorks word processing & spreadsheets. Draw documents retained objects as individual items but I did find that LO would quit or freeze when selecting those objects. Databases open as spreadsheets, losing any database functions but at least the data is there.

I am fortunate to have some older Macs available & keep a 2010 Mac mini running Snow Leopard for its ability to run PPC apps such as AppleWorks 6 & some other apps that just work better in Snow Leopard. I also have a G4 iMac (2004 or so vintage) running Tiger, Mac OS X 10.4.11, that can run Classic & can even boot into System 9 if I can find a bootable CD. I realize that not everyone is able to do this.

There's no contemporary app that fits it all since .cwk files can be arbitrarily complex in their structure.

My best solution: I installed SheepShaver (https://sheepshaver.cebix.net) and and run my old AppleWorks inside this virtual machine.

SheepShaver doesn't run right out of the box, as you have to get an old Classic OS CD image and an old ROM image first. But if you read the very helpful support and forum pages on https://www.emaculation.com carefully and follow the links, you should be able to find all that you need and put together a reliable, working ClassicOS.

Once you're done you can install Apple Works and open, edit, print and PDF all your precious .cwk files via the shared folder.

Good luck!

Try to open from inside TextEdit and see if there is text you can cut and paste out to somewhere more recent.