Every time I need to copy a file to my iPhone, it is a hair rising experience.  Why?  Why I need to use some third party software to do the most basic task there is?

I bought the very first iPhone (2G) in February 2008.  Somehow I figured out how to  to move media files between iPhone and PC.  It was clumsy and awkward.  It was a torture and menace.

And have to repeat this again.  Apple did not fix this problem till present.  Do the listen for people’s cry for help?  Apparently, they do not have ears.  It is still a pain in 2015 on iPhone 5S.  File management on iPhone is as terrible and awkward as it was 7 year ago.

This time I needed to copy over a hundred speech MP3 files to an iPhone.  I need something robust and automatic.

Concept

(01) Open something called iTunes

(02) Plugin your iPhone and click on it inside this software

02) Add your files to iTunes LIBRARY (press Alt, if you do not see File menu)

(03) Sync your iPhone with iTunes

Prerequisites

This example was tested on 2G iPhone with iTunes 10.1.1.4 on Windows 7 64-bit Ultimate.  This example later confirmed on iPhone 4S with iTunes 10.5.o.142.

To start you need iTunes installed somewhere on a disposable instance of Windows operating system.

Also, get ready to loose all music files that you already have on your iPhone.  Run a backup, but this step is very useless – it will restore you back, but where are your latest changes?

Step-By-Step Procedure

First, open iTunes.

Second, click on File – Add Folder to Library…

Navigate to a locations of your MP3 files and pick a required directory.

Third, when Sync-ing your iPhone, make sure that Music is selected for synchronization.