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I am trying to find/locate iMessages from a certain day back at the beginning of October. Is this possible? Scrolling back on the history on my iMac in Messages goes back to 10/19/15 but no further. On iPhone it is more recent than that.

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If it was archived on your Mac, you can find it by date.
Navigate to ~/Library/Containers/com.apple.iChat/Data/Library/Messages/Archive/
Open the relevant dated folder & any conversations for that day will be listed by the contact names.

Double-clicking will open it in Messages.

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    You rock! Thank you. This is exactly what I needed...and it was simple to get it done. – Sizzle Nov 20 '15 at 13:45
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The last I tried this was OS X Mountain Lion and iOS 6.x on a jailbroken device. There is a messages database located on each device. You can Google for the exact location in your OS versions.

I know these databases used to be SQLite, and you could browse the database using SQLite commands and see all info stored in the entire database.

Be sure to make a backup first, and ideally, do all your investigation in the backup database.

There also used to be a Cydia app that would allow you to search all of your iMessages by date/contact/etc., but the name escapes me at the moment.

This may not be the greatest answer, but it's all I've got, and at least it's something!

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