Step 2Make sure that the option 'Save history when conversations are closed' is checked. Open the Messages app and go to Preferences > General. Step 1You can choose where to save your chat history from the Messages app. Therefore, if you are using macOS later than Sierra and want to recover iMessages, give a cross-check to ensure that the messages have been saved on your Mac hard drive. On macOS High Sierra/Mojave/Catalina, you can decide whether to keep iMessages to your Mac hard disk or just storing them to iCloud. However, due to space consumption issues, this feature was altered to suit your preferences. Before macOS Sierra in 2016, all iMessages are stored on Mac hard drive by default. On macOS Sierra and earlier, all iMessages are stored on Mac hard drive by default. How to View Old iMessages on Mac from iCloud?.How to Restore Old iMessages from Time Machine?.How to Find Recently Deleted Albums on Mac?.