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For Obsidian, since it's an Electron app, it uses .asar patch files to do incremental updates. Would be difficult (impossible?) for Latest to read these.
If an update is indicated, it typically indicates a new "installer" version available which also updates the bundled Chrome engine etc. So it's always good to download the updated .dmg anyway even if you "already" have the latest version installed.
Latest should not show Obsidian as update as most recent version is already installed
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