Article
Ask iLounge 8-2-07
By Jesse David Hollington
Contributing Editor
Published: Thursday, August 2, 2007
Category: Ask iLounge
Ask iLounge offers readers the opportunity to get answers to their iPod-related questions from a member of the iLounge editorial team. We'll answer several questions here each week, and of course, you can always get help with more immediate concerns from the iLounge Discussion Forums. Submit your questions for consideration using our Ask iLounge Submit Form. We reserve the right to edit questions for grammar, spelling, and length.
How do I copy music from my iPod onto my computer?
Click here for the answer.
How do I put DVDs on my iPod?
For converting DVDs, web video, TV shows and home movies to your iPod, iPhone or Apple TV, we have a three-part series outlining the best formats, settings, and various tools to use for converting all types of video content for use on these devices.
The Complete Guide to iPod, iPhone and Apple TV Video Conversion (Mac)
The Complete Guide to iPod, iPhone and Apple TV Video Conversion (Windows)
Q: What are the best speakers to use with my iPod? (15, 76-79, and 90-92)
Q: What are the best headphones to use with my iPod? (10, 72-75, and 90-92)
Q: I really want to get a nice case for my iPod. Do you have any suggestions? (36-37, 54-67, and 90-92)
Q: How can I connect my iPod to my car stereo? (14, 32-35, 68-71, and 90-92)
Q: Are there any batteries that I can use to extend my iPod's battery life? (82-83 and 90-92)
A: Answers to these and many other questions can be found in two places. Our Free iPod Book 3.3 provides a complete report card to all of the iPod accessories we've reviewed as of summer 2007, as well as over 125 iTunes and iPod tips & tricks. Further, our new 2008 iPod & iPhone Buyers' Guide has accessory tutorials at the page numbers listed in parentheses above. These and other publications in our Library are free downloads, developed by the editors of iLounge!
Each week we receive numerous inquiries asking the same very common questions such as “How Do I Copy Music From My iPod Back to My Computer? and “How Do I Put DVDs on my iPod video?”
Although we have had tutorials on these subjects for some time, over the past few days we’ve been updating and revising these tutorials to ensure that we have included all of the current tips and tricks and the various software tools that are available.
If you’re looking to copy content from your iPod back to your computer, including music, movies, and even games and photos, be sure to check out:
For converting DVDs, web video, TV shows and home movies to your iPod, iPhone or Apple TV, we now have a three-part series outlining the best formats, settings, and various tools to use for converting all types of video content for use on these devices.
Part 2: The Complete Guide to iPod, iPhone and Apple TV Video Conversion (Mac)
Part 3: The Complete Guide to iPod, iPhone and Apple TV Video Conversion (Windows)
Q: I’m about to get an iPhone that I will use mainly for personal use, but will probably start using for work as well (ie, for contacts, calendars, and e-mail). Should I setup the iPhone on my Windows PC at work rather than on my Intel iMac at home? I know that Windows-formatted iPods can connect to iTunes on a Mac just fine, but wasn’t sure about the iPhone.
- Matt
A: Actually, with the iPhone there are no “format” issues like there are with the iPod models. Since the iPhone now uses a synchronization protocol with iTunes that is not based on any kind of “disk mode” access, there are no compatibility issues with using the iPhone on both a Mac and a Windows computer. You can therefore set the iPhone up on either your iMac at home or your Windows PC at work, and it can be synchronized to either machine.
However, it is important to note that the iPhone is not currently designed to synchronize the same content with multiple computers, so you will not be able to sync your contacts to both machines, or load music or podcasts from either machine. This is exacerbated by the lack of any kind of “Manual” mode for the iPhone as well, meaning you can’t even drag in a single track or two from a secondary computer.
What you can do, however, is sync your music and video content from your iMac at home, and then sync your information such contacts and calendars from your Windows PC at work. This would allow you to have your work-based calendar and contact information, but not have to manage a media library on your work PC.
To do this, simply connect the iPhone to your iMac and select the appropriate synchronization options for your media content, but leave the settings on the “Info” tab alone until you get to your work computer. When you later connect your iPhone to your work PC, you will notice that none of the synchronization options are selected. From here, you can simply go in and select the options on the “Info” tab to collect your calendar, contacts, and any other information you want to sync from your work PC, such as bookmarks. You won’t be able to add music, podcasts, photos or videos to your iPhone from your work computer without replacing the content already on the iPhone, but you can easily move the iPhone back and forth between the two computers, and it will remember which content is being synced from which machine.
The bottom line is that all synchronization settings are handled independently of each other, and unlike an iPod, iTunes will not bother you with any warning messages unless you actually try to select content that is already being synchronized with another computer.
If you do try to synchronize media content (ie, music, podcasts, photos or videos) that has already been synchronized from another computer, iTunes will warn you that doing so will replace existing content:

On the other hand, if you try to synchronize calendars, contacts, or bookmarks when the iPhone already contains data from another computer, iTunes will instead offer you the option to either merge the content already on the iPhone with the content on your computer (in which case content from the iPhone will be added to your computer, and vice-versa), or to erase the content on the iPhone and replace it with the content from your computer:

Note that in terms of e-mail, there are really no synchronization issues to be concerned with. The iPhone does not synchronize e-mail content via iTunes, but merely your e-mail account settings, mostly just as a convenience to get you started. These can be setup directly on the iPhone with little additional effort, so you can safely ignore any e-mail synchronization settings in iTunes if you prefer and just configure your accounts manually on the iPhone from within the Settings, Mail menu.
Q: My boss uses his wife’s iTunes account to purchase music. He recently purchased some songs from iTunes and wants to move them as MP3 files to go onto his Blackberry. Upon trying to drop and drag into the Blackberry folder, he gets a notification for Optimum conversion, Advanced conversion, and one other one. Each time he tries to do this, he gets a notification that there’s nothing in the new folder for his Blackbery. I see that the purchased songs come into the folder as M4A format. How can he get these purchased songs to be MP3 files so he can put them on any MP3 player?
- Jeremy
A: Unfortunately, most tracks purchased from the iTunes Store are still protected by digital rights management (DRM) restrictions, which prevent you from playing them on a non-Apple device or converting them directly to another format such as MP3.
The exception to this are the newer “iTunes Plus” tracks available from certain artists on the iTunes Store. These are sold in a much higher bit-rate (256kbps versus 128kbps), and are free of any DRM restrictions. You can therefore convert these to MP3, or simply transfer the M4A files directly to the Blackberry (which should support that format directly as well).
Normally, purchased DRM-protected tracks will have an M4P extension, although this is not necessarily always the case, since the files can be renamed. You can tell for certain if a track is DRM-protected by viewing its properties in iTunes. To do this, select the track in question and choose File, Get Info from within iTunes. On the “Summary” tab of a music track’s properties, the “Kind” will indicate what type of audio file you are working with:

Normally, this will be one of the following four types for a music track:
- Protected AAC Audio File: AAC audio format, purchased from the iTunes Store, DRM-protected
- Purchased AAC Audio File: AAC audio format, purchased from the iTunes Store, unprotected
- AAC Audio File: AAC audio format from another source (ie, imported from an audio CD), unprotected
- MPEG Audio File: MP3 audio format, unprotected.
With the exception of Protected AAC Audio File content, any of the other types can be synchronized to a newer-model Blackberry device (such as the 8800, Pearl, or Curve) without any further conversion required. The newer Blackberry devices provide full support for the AAC audio format.
If you are in fact dealing with Protected AAC files, the only way to convert them for playback on a non-Apple device is to burn them to an audio CD, and then re-import the audio CD into a format such as MP3, as you would any commercial audio CD, using either iTunes or any other third-party CD “ripping” software.
Q: My 5G ipod will allow me to add video I downloaded from the internet, and it will allow me to add it to my Ipod, but when I play it from a playlist it will only play if I select a specific track, not continuosly, like the videos I download from the iTunes Store. Why is that?
- Robert
A: The most likely cause of this is that the “Skip when Shuffling” option is enabled for these video tracks, which can be found in the track properties by selecting the track and choosing File, Get Info from the menu and then choosing the “Options” tab:

When this option is enabled for a given track, the iPod will never play that track next in sequence when the “Shuffle” setting is enabled on the iPod (which can be found in the iPod’s Settings menu). The solution is to either turn Shuffle OFF on the iPod itself, or disable the “Skip when Shuffling” setting for these tracks. This can be done on a track-by-track basis (as above), or for a group of tracks by selecting multiple tracks before choosing the File, Get Info option:

Q: I bought the new 80 GB ipod and uploaded my songs into the iTunes library. I can listen to them all but I cannot edit the track tags at all. Every song is grayed out. Any ideas?
- Christine
A: The normal cause of this is that the audio files themselves are either stored on a read-only media such as a CD or DVD, or they are still marked as “read-only” in the underlying operating system. This will prevent iTunes from updating information within the file tags themselves, and therefore iTunes does not let you edit this information at all.
In Windows, often when files are copied from a read-only media source (such as a CD or DVD), they retain the read-only flag unless it is reset manually.
You can check this by going to the underlying file and examining its properties from within Windows. The fastest way to do this is to select the tracks within the iTunes library, and right-click on them and choose “Show in Windows Explorer” from the context menu:

This will open a Windows Explorer window with the file in question highlighted. You can then right-click on the file from within Windows Explorer and choose “Properties” to examine the file’s properties:

If the “Read-only” box is checked, this indicates that the file has been flagged as read-only by the underlying operating system, and iTunes will therefore not be able to update it. If this is the case, simply UNcheck the “Read-only” checkbox, and click OK to save the file.
You can also do this for multiple files simply by selecting them all and choosing File, Properties from Windows Explorer. This change can even by applied to an entire subdirectory tree by choosing the top-level folder and selecting File, Properties. In this case, simply UNcheck the “Read-only” checkbox, and when clicking OK you will be prompted as to whether you want to apply changes to the current folder only, or to all sub-folders:

Therefore, if you find that the majority of your files are in fact set as read-only, you can simply select the top-level “iTunes” folder (located under “My Music"), and change the Read-only flag at that level to set it on all files in your music library.
If you are using a Mac instead of a Windows computer, this problem is less common, but can still occur if the files are “Locked.” The same basic principles apply as above, except you will be looking for a “Locked” checkbox rather than a “Read-only” checkbox:

Q: My MacBook’s hard drive just died and all of my music, music videos, photos, addresses etc. are on my iPhone. I know there’s a tutorial for this problem for the iPod but how do I get everything off my iPhone and back onto my computer?! Please help!!
- Anonymous
A: The iPhone uses a new synchronization protocol that is different from the iPod line of devices. Unfortunately this means that there are presently no third-party tools that can be used to recover any content from the iPhone, nor is there any kind of “Disk Mode” available that would allow manual access to this data.
Content purchased from the iTunes Store can be transferred back from the iPhone via iTunes, in the same way that it can for the iPod, using the “Transfer Purchases” option in iTunes, as described in our article, Copying Content from your iPod to your Computer - The Definitive Guide. Unfortunately, however, this will not help for music and video content that was imported or acquired from other sources.
The only other information that can be recovered from the iPhone are the contacts, calendars, and bookmark information. Since iTunes provides bi-directional synchronization of this content, connecting the iPhone to your computer and selecting the “Merge” option when prompted will transfer all of the content from your iPhone’s contacts, calendar and bookmarks back to the appropriate applications on your computer:

One last rather tedious option does exist for recovering photos from the iPhone, and that is simply to e-mail them to yourself. This may not be practical if you have a lot of photos, since they will need to be sent one at a time, but it is a far better option than losing your photos altogether.
Q: Does the iPhone play video through it’s dock connector? It appears the iPhone dock is an audio only output. Can I place the iPhone in the Universal Dock to play videos through either it’s composite or s-video connector? Does video play out of the headset port like in the iPod video?
- Chrystopher
Unfortunately, the iPhone does not offer any kind of video output capabilities at all, through either the Dock Connector or the headphone port.
Connecting video playback accessories to the Dock Connector port will generally provide audio playback, but no video output as the iPhone simply does not provide a signal through this port.
With regards to the headphone port, the third connector is actually used for the iPhone’s headset microphone input, and therefore connecting a standard iPod video cable to a TV would not only provide no video output, but in fact could conceivably damage the iPhone, since the yellow lead would be mapped to the microphone input, rather than a video output.
Whether this feature has been permanently eliminated, or whether it will be added in a future firmware update is uncertain at this point. However, it is important to note that the iPhone has been designed as a multi-purpose device with an emphasis on phone and Internet features, and therefore this may be an omission based on the nature of the device itself. Whether or not a next-generation iPod will continue to provide this capability is equally uncertain, but the feature set of the iPhone should probably not be taken as any indication.
The fifth-generation iPod, of course, continues to support video output through either the Dock Connector or the headphone port, and the Apple TV is certainly an option if you will frequently be watching videos on a TV. Both of these devices provide significantly greater storage capacity than the iPhone, and all will synchronize video playback tracking information such as last played time, play count, and even bookmarked playback position between all three devices via iTunes.
Q: I am unable to send or receive picture (or video) messages on my iphone. Is this normal? Shouldn’t a device as sophisticated as the iPhone be able to send and receive picture messages? It seems like such an odd omission that I have to assume that I’m missing something.
- Katherine
Unfortunately, the answer is no. The iPhone does not presently support Multimedia Messaging Services (MMS), which is normally required to support picture and video messaging services. Only basic text messaging (SMS) is supported.
You can send and receive photos with the iPhone via e-mail, of course, using your default e-mail account (as specified under Settings, Mail, Default Account). Further, many cell phone carriers do provide e-mail to MMS gateways, which normally take the form of the recipient’s cell phone number followed by the carrier’s MMS gateway domain. For example, to send a message to somebody on the T-Mobile network you would send it as an e-mail to a number such as 9175551212 @ tmomail.net. A user in our iLounge Discussion Forums has created a helpful post with common MMS gateways for U.S. carriers listed in the thread How to SEND MMS from the iPhone.
Likewise, many carriers also offer the ability to send MMS messages to an e-mail address. If you wish to receive picture messages on your iPhone, the sender should be able to simply address the message to your normal e-mail account, which the iPhone will download as it would a normal e-mail message.
Ask iLounge Archives:
5-16-08: Using the iPhone with integrated in-car Bluetooth, Problems with iPods and depleted batteries, Transferring content to a new iPod, iPod displays audio but no video, Removing photos and album artwork from iTunes, Overdrive Media and iPods
5-9-08: About iPod battery life and charging, Using Apple FM Radio remote on older iPod models, Scan and Fix dialog using iPod on Windows Vista, Preserving iTunes metadata when reinstalling Windows, Importing multiple tracks into iTunes, About iTunes and ID3 tags
5-2-08: Transferring digital camera movies to iPod, Reordering and shuffling playlists, Transferring playlists between iTunes libraries, Importing audiobooks, Correcting tags on CD import, Burning CDs with longer gaps
4-25-08: Finding Duplicates in iTunes, Setting files to open in iTunes automatically, Resetting authorizations, 1G iPod nano and voice recording, Syncing a library larger than your iPod capacity, Grouping multi-disc albums
4-17-08: Ripping CDs to external hard drive, Zeppelin speakers and USB port, Bluetooth stereo on iPhone, Converting TV shows to iPod, Audio recording on iPod touch, Wireless security on iPod touch
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1
regarding the question about transferring content from the iPhone, “One last rather tedious option does exist for recovering photos from the iPhone, and that is simply to e-mail them to yourself. “
When I plug my iPhone into the computer (PC), it automatically prompts me to use the ‘scanners and camera’ software to download the full-res pictures off the iPhone.
if you email your pictures, it will send a low res version.
(this applies to the pictures that your iPhone took with it’s 2MP camera)
Posted by dabido on August 16, 2007 at 6:41 PM (PDT)