I have been a long-time listener to Steve Gibson and Leo Laporte’s podcast, Security Now. I think it’s a great podcast to listen to for people who have an interest in computer security. Since it’s one of my concentrations in my Master’s in Computer and Information Science degree, it’s a perfect fit. I only wish I had discovered it before I took a lot of the classes. I would have understood even more and been able to apply the knowledge to learn even more. I highly recommend listening to the podcast from the beginning episodes if you’re a beginning computer science student with an interest in security (and if you have the time). I listen to it in the car and a lot of times while taking a shower, doing the dishes, cutting the grass, or some other mindless task.
I’m back in the 2011 episodes which I get from Steve’s site at GRC. For a long time, I’ve been able to download the podcast episodes, import them to iTunes, set the media kind as podcast, check the “Remember playback position” box, and sync the podcast to my iPhone 5. Having stopped listening for a bit and coming back to it on my iPhone 6, I find it’s only syncing one episode instead of five. I have the options in iTunes set to sync the “5 least recently unplayed episodes” but it persistently only shows one on the phone itself. To make it worse, the title shown and the podcast that play aren’t the same. iTunes says the phone has all five episodes when I look but the phone insists it only has one episode. That’s very annoying.
I read a few articles online looking for help and found one that gave me an idea. It was a discussion thread on Apple’s site. A user suggested changing the podcast to an audiobook and play it from there. I tried it with 6 episodes, synced them, and found it worked just fine. Another user switched them back and forth between podcast and audiobook and found that trick worked. I then changed them back to podcasts, synced again, and found the five episodes that should have been there. Success!
In summary, the only thing I did was change the media kind to audiobooks, synced, changed the media kind back to podcasts, and synced again. I have no idea why it works but at least it did. Before discovering this, I’ve had to sync only one episode at a time which meant I had to resync after each episode. That got old fast. I hope this helps you.