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What you're asking for was never possible in any version of iTunes, and isn't suported now either. That's why some apps have a built-in option to transfer files using their own methods (like &quot;WiFi transfer&quot; that you mentioned).<br />
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The only other way to do it is to use iCloud Drive. Anything you put in it on your PC can be accessed on your iPad, and any apps that support it, will see those files as well.
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What you're asking for was never possible in any version of iTunes, and isn't suported now either. That's why some apps have a built-in option to transfer files using their own methods (like "WiFi transfer" that you mentioned).

The only other way to do it is to use iCloud Drive. Anything you put in it on your PC can be accessed on your iPad, and any apps that support it, will see those files as well.

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If you see the image here (downloaded from google), I was referring to marked section 4 which is how it used to appear in earlier versions of iTunes.<br />
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<a href="https://filedb.experts-exchange.com/incoming/2015/02_w06/895592/iTunes.png" target="_blank" title="Inserting files into applications through iTunes (415 KB)"><img alt="Inserting files into applications through iTunes" class="file-block lazyload" style="max-width: 800px;" data-src="https://filedb.experts-exchange.com/incoming/2015/02_w06/800_895592/iTunes.png" /></a>
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If you see the image here (downloaded from google), I was referring to marked section 4 which is how it used to appear in earlier versions of iTunes.

Inserting files into applications through iTuneshttps://filedb.experts-exchange.com/incoming/2015/02_w06/895592/iTunes.png

Inserting files into applications through iTunes

iTunes.png

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I am somehow not able to see the file sharing with the combination of latest IOS and itunes. Anyway, I am closing this for now as I have decided to use third party tools.
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I am somehow not able to see the file sharing with the combination of latest IOS and itunes. Anyway, I am closing this for now as I have decided to use third party tools.

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I have the latest version of iTunes on my laptop and the latest version of IOS on my iPad2. In earlier versions of iTunes, I remember transferring files to applications (like Adobe Reader, GoodReader, etc) by clicking on the application in 'My Apps' and adding files (pdf files) to it. Somehow, with the latest version, I am not able to do that. Is there a way to do it other than enabling 'WiFi Transfer' from within the app?
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I have the latest version of iTunes on my laptop and the latest version of IOS on my iPad2. In earlier versions of iTunes, I remember transferring files to applications (like Adobe Reader, GoodReader, etc) by clicking on the application in 'My Apps' and adding files (pdf files) to it. Somehow, with the latest version, I am not able to do that. Is there a way to do it other than enabling 'WiFi Transfer' from within the app?

How to copy files to an IOS app through iTunes

iPad is an iOS-based line of tablet computers built around the device's multi-touch screen, including a virtual keyboard. The iPad includes built-in Wi-Fi and cellular connectivity on select models. An iPad can shoot video, take photos, play music, and perform Internet functions such as web-browsing and emailing. Other functions – games, reference, GPS navigation, social networking, etc. – can be enabled by downloading and installing apps.

iPad

Programs written for the Apple operating systems are distinguished from software created for other operating systems in that it must be approved by Apple for use on its devices, whether it is from Apple (Final Cut, iWork, Keynote, Logic Pro and GarageBand are popular titles), or is a third party application from Parallels, Nuance, Microsoft and Amazon, among many others.

Apple Software

iOS is a mobile operating system developed by Apple; it is a derivative of the Mac OS X desktop operating system, with which it shares many (but not all) common frameworks and other components. These include Cocoa Touch, the Mach/Darwin/XNU kernel and code from the Berkeley Software Distribution (BSD). Each iOS application runs in its own secure sandbox to prevent altering other applications, the operating system, or any other data.