Is Mac version 4.4.3 compatible with iOS version 5.3?
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No there should be no incompatibilities. They use the same data format. Many users as still running Mavericks so it would not make sense to not ensure backwards compatibility with it.
Since you mentioned you would like to sync via Dropbox. You have the option to use the trial version from the 1Password website.
I would like to note the iOS version is free unless you want the additional Pro features and its available through the iTunes store. There is a free trial (30 days fully functional) from the website here for the Mac version. So really you have nothing to fear. You can download them both and use the features to make sure they suit your needs before ever needing to spend a penny.
Thats the way I did it so many years ago, of course it wasn't 2 maybe 3 days into my trial I already knew it was for me and purchased it right away. As to the iOS Pro features they are available through an In App Purchase at any time. Details on the Pro features can be found here https://guides.agilebits.com/1password-ios-kb/5/en/topic/pro-features-faq
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Quick note that since you are on Mavericks you will have to use 1PW4. This can be downloaded from the Legacy section of the Downloads page.
As for the license, the same license works for 1PW4 and 1PW5, so just go ahead and buy the license for 1PW5.
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Thanks @danco for catching that.
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@jpcirrus: I'll also add that you can actually purchase 1Password from the Mac App Store as well, but as the current version (5) is Yosemite-only the purchase would need to be made on a Yosemite Mac. However, once you have purchased 1Password 5 from MAS, your Macs running Mavericks can still download 1Password 4 from your MAS purchase history.
Just be aware that iCloud Sync requires 1Password 5 from MAS running on Yosemite (as well as 1Password 5 on iOS 8), so Dropbox is the best option for syncing between multiple OSes (including Windows, Android, and even older versions of OS X and iOS). I hope this helps! :)
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