How Do I Transfer Songs From iTunes to iPod Touch (5th Gen)?

Thanks for the comeback, Jeremy. I hope you will stay with me and help me work through this.

Let's try the first solution mentioned - manually adding items to my device (iPod). OK - I have the latest version of iTunes (V. 12.6.1.25). I have my iPod connected to a USB port and iTunes is recognizing it. "Mike's iPod" is listed in the left-hand column and there is a very small, iPod icon in the upper left area of the iTunes window. I make sure my iTunes library is in the main window - not my iPod music. I then select the song I want to copy. I left click on it and drag it over to "Mike's iPod." As I hover the cursor, it blinks, indicating (to me anyway) that the song will be copied onto the iPod when I release the mouse (same as copying a song into a playlist). I release the mouse. I go to my iPod. The song has not been copied. It isn't there.

Am I leaving anything out or doing anything wrong?

There is another way to manually do it that is not mentioned in the article. I select the song I want and then right click on it. A menu pops up inviting me to "Add to Device." The extension of that menu item says "Mike's iPod." You would think, wouldn't you? But no, of course not. Doesn't do diddily. I click on it and nothing gets added to the iPod.

Second suggested solution to follow ....

The other solution suggest involves synching. I did all the steps there exactly as described in the article. With the iPod connected to my computer and iTunes open and recognizing the iPod, I clicked on the iPod icon in the upper left, which took me to the Summary Screen. I scrolled down to Options and checked the box next to "Manually manage music and videos," leaving the rest of the boxes under Options unchecked. I then clicked on Apply. Nothing happened. So I clicked on Synch. At the top of the screen, it told me synching was taking place. That's all I saw. It happened very quickly, then it was over. I went to my iPod. Nothing.

??????

I just noticed something. There is an exclamation point just to the left of the song title. At this point, I should tell you that the "song" I am talking about is actually a two-hour episode of "A Prairie Home Companion" which I transferred from a cassette tape onto my hard disk using a cassette capture device and Audacity software. I then imported it into iTunes as an MP3 file. It is in iTunes on my computer and I can play it just fine. It just doesn't want to transfer to my iPod.

I have done this before with other episodes of "A Prairie Home Companion" and transferred them to my iPod without any trouble. I suspect it's the exclamation point that is holding things up here.

I can right click on the "song" in my iTunes library, click on "Get Info" and the Information window pops up. That's where I'm at right now.

Thoughts?

I got rid of the exclamation point by moving the file into my iTunes music directory. Why it wasn't in there to begin with I don't know, because I had imported it into my iTunes library earlier. Oh well.

In any event, it doesn't make any difference. I am still unable to move the song from iTunes on my computer, onto my iPod. What now?

Thank you. The support link led me to a chat session that resulted in solving my problem. Turns out, I was just not synching correctly. Once I did that, the song hopped right onto my iPod. So we killed two birds with one stone - my immediate problem got solved and I also now know how to synch properly!