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I use iTunes File Sharing (on Windows) to share a password file with an iOS app KeePassMini.

I am not sure if this is a one-time thing or if iTunes copies the files whenever it changes.

Ideally, iTunes would copy the file back from the device if it was changed on the device and copy it again to the device if the file was changed on the client.

In case of a conflict either the older file should be overwritten, or the action set that always the device "wins". Or alternatively just ask the user.

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    The file sharing feature is not a sync option, but meant to place a file into an app manually supporting this feature. Once the app is opened on the iOS device, it is then available and handled according to the way outlined by the app developer. This can be that you can get a copy back later on using the same feature in reverse or it can be that the file is removed from that file sharing location, which makes exporting it again impossible. Examples for comparison are: Numbers (import/export of documents possible) and TeamSpeak (export of identities, which can be imported, not possible). – Phoenix Apr 27 '16 at 7:22
  • So once I add the file in iTunes it "forgets" the link to the original file on the PC? Pretty disappointing :-( The App I mean (MiniKeePass) seems to apply modifications and lets me export it again. But this is a pain doing manually. Is there at least a way to add a file (overwriting the current one) and saving one in a programmatic, external way? E.g. command line arguments etc? – divB Apr 27 '16 at 8:02
  • As I said: The iTunes File Sharing feature is for manually importing/exporting files. Contrary to a synchronization, there are no records as to where a file came from or which is more up-to-date. Since I do not have the app in question, I would not know how it behaves internally. This would be a question to the developer. If the file is offered for export, you'll get a file save dialog on where to save the file. If another file with the same name and different date stamp is found, you are asked to replace the file. In other words: By default it does not use a different filename. – Phoenix Apr 27 '16 at 8:31
  • Yes, I understand. Forget about the name etc. My question is if I can automate the Export/Import thing with an external script. Doing this manually every single time is 70ies ... – divB Apr 27 '16 at 8:42
  • The simple answer is "no". File Sharing was the first option Apple provided in iTunes to transmit 3rd party files to and from an installed app on the iOS device. This particular way of transmitting a file is a manual process. In the meantime, there are several apps which allow other means of file transfer and syncing. Be it over a proprietary server, iCloud (Drive) or directly to your computer. If your app does not have other means than iTunes File Sharing, the process remains "70ies" style to put it in your terms. – Phoenix Apr 27 '16 at 9:47
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The iTunes File Sharing feature was the first option Apple supplied to allow manual transferring of files to installed 3rd party iOS apps, which support that feature. The main reason was (and still is) to put documents into an app or get them out again.

The handling of uploaded (imported) files is wholly controlled by the app allowing this feature.

As a comparison:

  • Numbers (by Apple):
    • Allows files to be uploaded
    • Uploaded documents will be moved to a place inside the app outside the reach of iTunes File Sharing, but can be placed back for retrieval (e.g. after having worked on them on the go)
  • TeamSpeak (by TeamSpeak Systems GmbH):
    • Allows to upload identities to be used with servers you like to connect to
    • Once placed in there, the file will be read and worked on upon start of the app and removed from the upload location, disallowing any identities to be extracted

Since this feature was not meant to synchronize files from inside the app with versions outside the app (e.g. on the computer), there is no synchronization databank holding records of file information in order to determine which is newer.

Furthermore, iTunes is limited on what one can do with a script to automate processes. Utilizing the File Sharing feature is not among the scriptable parts of iTunes.

Due to the lack of features, many app developers (including Apple) expanded to use different means to transfer files and even synchronize them. Many apps, if they do not use SMB, AFP or WebDAV (HTTP), use their own propriety server system to synchronize across devices.

With the introduction of iCloud, Apple allows even 3rd party apps to sync in-app content. This feature needs to be supported by the app itself to make use of it.

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