Ask TUAW: shuffle by album and AirPlay from iOS, plus lots of iCloud questions

Welcome to Ask TUAW, our weekly (mostly) question-and-answer column. This week we're again hitting a ton of questions about iCloud and iOS 5.

By the way, we can never have too many questions. You can't have a Q&A column without the Q, so please go to the comments of this post and ask away. Believe it or not, we've had a little bit of a drought of questions, so now's your chance to get them answered! If you prefer, instead of asking questions in the comments, you can also email your questions directly to ask [at] tuaw.com, or simply ping us on Twitter.

For our first question, Guillaume asks:

Does the Music (née iPod) app in iOS 5 have a "shuffle by album" feature, rather than just "shuffle by song" like currently? On my old first generation iPod nano, or in iTunes, I can play albums at random. This is not possible on my iPhone. I can only play songs at random, and it doesn't make for a very pleasant experience if you jump into the middle of a classical concerto and then to a song from a rock concert.

Great question. I've done some poking around in iOS 5 and haven't found an option for "shuffle by album." That doesn't mean it won't be in the final version, but it isn't somewhere immediately obvious. However, I did find a possible solution to your problem.

Smart Shuffle, a free iPhone/iPad app from Spudfish Software, does exactly what you ask. From the description: "Do you miss the old "Album Shuffle" on your iPhone or iPod touch? Here at Spudfish Software, we did, so we did something about it!" It's not as simple as a built-in "shuffle by album" button, but it should get the job done. Best of luck with your classical concerto/rock concert conflicts!

Tom asks:

I signed up for the MobileMe trial. Will I get it free for a year?

Maybe! Check your MobileMe account page for your expiration date. If it says June 30, 2012, as mine does, you are all set!

Stuart wonders:

What about new Macs that were ordered prior to June 6, but being delivered early July? For example, new iMacs with the SSD option? Am I expected to pay another wad for Lion?

Typically, Apple considers a computer "purchased" when it is delivered. Once your machine arrives and Lion is released, check Apple's OS X Lion Up to Date page for information on how to claim your free copy of Lion. If your machine takes long enough to arrive, it might even come with Lion pre-loaded! If you receive your machine after June 6, I think you'll be just fine.

May has a quick question about email attachments on the iPad:

How do I insert or attach a doc (of any kind) into an email which I send out for my iPad? I can't seem to be be able to find such an "insert attachment" function within the email of iPad.

The iPad Mail app doesn't work that way. Instead of bringing attachments into Mail, ignoring what app they come from, you have to go into individual apps and send documents to the Mail program. It's part of Apple's strategy to eliminate the file system.

Apple feels that it doesn't make sense to open the Mail program to share a file. Instead, you should go into Pages or the Photos app and choose the file you wish to share. It's focused on the documents themselves, rather than the action of mailing them.

It's a different -- and theoretically more intuitive -- way of managing files. Get the document, then execute the task, rather than the other way around.

In your case, open up the app that contains the document you wish to send (in Pages, DocsToGo, or wherever) and tap the appropriate button to email the file. It should transfer to a new Mail message that you can send off as you wish. It's a little different than on the Mac, but it makes sense once you do it a few times.

Anchal asks a number of iCloud questions, none of which I have great answers for. They've all been asked, in one form or another, a few times over the past week, so I'll just throw them all out there:

Since iCloud will only store 30 days worth of photos, do you know if there will be functionality to access photos from your computer via the Web?

In general, will there be web access to iCloud content? (If you could access music via Web, then Apple would be killin' it.)

How exactly is iTunes matching music? Does it compare audio samples or just ID3 tags?

After you match a set of songs in iTunes, and you add more songs (that you did not get through iTunes), will it remember which ones it already matched and just match the new ones?

Have there been reports on speed comparisons of syncing via wireless vs USB?

I'll hit these one at a time.

With regards to web access of iCloud content, we don't have any concrete answers, but MobileMe has excellent web apps for mail, contacts and calendars. I have no doubt those will continue to exist (although opinions differ on that point).

Accessing the 30 days of Photo Stream photos might be doable in a similar way to the current MobileMe Gallery, but with MobileMe web hosting rumored to be disappearing, the Gallery function might be gone, too. We'll have to wait until closer to the official iCloud launch in the fall to know for sure.

I am nearly positive that you will not be able to access iTunes Match music via the Web. I could be wrong, but it is designed to sync all data across your devices, not every device you might happen to use. Again, we'll have to wait until the iTunes Match launch in the fall.

Regarding the actual matching of songs in iTunes Match, we don't have the full story yet, but I suspect it will be a combination of audio samples and metadata. I highly doubt that you'll be able to rotate metadata on songs and download whatever you want. It'll need some audio-matching as well. Most likely it is based on Apple's acquisition of Lala, which implies it's both metadata and music 'fingerprinting.'

Syncing via USB is almost 100 percent guaranteed to be faster than syncing via wireless. However, because the wireless sync is designed to run at night, while the phone is charging, the speed shouldn't matter too much.

Robert has a couple more iCloud related questions:

How much of my content (if any) will be accessible from the Web (i.e., not on a Mac that I own)? I'd love to listen to my music library at work. My iPhone only stores so much. (I have a Google Music account, I could always upload there.)

WHAT I REALLY WANT is to take a picture on my iPhone, have it loaded to the Web (and synced across devices - but this is less important), and then posted to my Facebook profile automagically, and then give me a link I can send to my mom that she can click on and see the pictures without logging in or any of that crapola. Is this going to be in iCloud? Is there already "an app for that?"

Your first question is pretty similar to Anchal's above. It seems pretty unlikely to me that iTunes in the Cloud users will be able to access their music through the Web. The service is meant to sync data across your devices, not via the Web. Time will tell on that, however.

What iTunes in the Cloud WILL let you do is delete and add songs to your iPhone at your leisure. If your iPhone is full of music, and you have a hankering for something that's in your iCloud account and not on your iPhone, you can delete some music from your iPhone (something that can't be done currently, and remember, all of your music is backed up, so you can safely delete your songs all willy-nilly) and immediately download whatever songs you want, for free.

As far as your "take a picture, upload it to Facebook and send it to Mom" question, your best bet is to use the Facebook for iPhone app to take your picture and upload it to Facebook. Once Photo Stream comes out, that photo you take from within the FB app will automatically get sent to your Photo Stream and get uploaded to Facebook for your mom to see.

Best of luck to everyone, and I'm sorry I don't have all the iCloud answers. Check back this fall for more concrete answers regarding iCloud, once we are closer to the official launch and release of iOS 5. Until then, most iCloud answers are going to be mostly conjecture.

Anyway, thanks for the questions everyone, and remember: it's tough to have a Q&A column without Qs. So, put your questions in the comments of this post, or shoot us an email at ask [at] tuaw.com. Also, if you have anything to add to our answers, we love feedback and fresh ideas.

Seriously, we want questions! Now, have a great week!