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I have some work with Captivate 4 & 5. Will they work with Captivate 9
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Sorry, but I expect big upgrade problems, certainly from CP4. It will be almost impossible, you'll need to find an intermediate version, but even if you upgrade in two steps, the result is at thte least unpredictable. Personally I would recreate the projects.
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Will these old projects work with Captivate 4 and Captivate 5?
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You can certainly build or update a project with CP4 and 5.
You won't be able to output HTML5 content, just SWF.
If you then need to upgrade those projects to CP9, that's where Lieve warns you - that drastic an upgrade will likely cause problems.
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I doubt that you will be able to upgrade your Cp4 projects directly to Cp9. From memory, you first needed to upgrade them to something like Cp5 or 6, so that they became a CPTX file before you could migrate any further upwards. The same may apply to Cp5, but since those were already CPTX, you might get away with it. But as others have said, even when successfully migrated to Cp9 format there will usually be quite a lot of rework and tweaking required.