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iOS On The Road: Using Siri in the Car

Images Courtesy of Jawbone and Apple

I have done a lot of traveling by car as part of my job for the last four years, so it is pretty natural that I have learned over this time how to adapt my iOS usage to suit my needs on the road. For example, I’ve done several reviews of GPS apps (just search here. There are several.) over the last two years thanks to my ample opportunities for field testing. As much as I enjoy taking navigation apps for a spin, however, with the release of iOS 5 and some new road-friendly features, it seems like a good time to branch out and go beyond just GPS. So, I will be working on a series of articles called iOS On The Road, featuring some of the tips, tricks, and helpful apps I have learned about and picked up while using iOS on the go over the last few years.

What better way to start this new series than with Apple’s latest and greatest new toy- Siri. As soon as I heard about what Siri would offer during the iOS 5 announcement, I got really excited. Here was a tool that was perfectly geared toward the road warrior. Not only was it an integrated way to dictate text to the iPhone, but to also interact directly with it in a conversational way to get information out. I knew this could definitely change the way I spend my time in the car.

Speaking of which, this is not the first time I have tried getting things done (safely, mind you) while driving. Unfortunately, my experiences of the past few few years often started out promising, but ultimately ended in disappointment. I’ve tried all of the big apps available for iOS. Unfortunately, while most of them work quite well in a quiet environment, you don’t always have that luxury while driving. Also, since I use my iPhone for podcasts, music, and GPS while on the go, it stays docked in the car, and is plugged into my vehicle’s included AUX jack. Having the iPhone away from your mouth makes dictation, no matter what the app, a nightmare.

I used to keep my iPhone jailbroken as much as possible, and there was a hack for SBSettings that would force all audio through to your Bluetooth headset, even if it didn’t have A2DP. I tried using this with Dragon Search and Dictation, Jott, ReQall, and Vlingo, but ultimately with very little success. The fidelity and consistency of operation just wasn’t good enough to rely on.

Eventually, several of these apps were updated to work natively with Bluetooth headsets, but even then, they just didn’t work well enough to be worth the trouble to use. There were always too many mistakes to correct, and I couldn’t rely on the headset to work every time I pushed the button. Between hardware hiccups and typos, if you’re constantly having to pay attention to the app, or press the screen to copy or paste text or do whatever else, is that really any safer than just typing a text using the keyboard? Unfortunately, not really. (And just for the record, I am NOT condoning or recommending that practice.)

Ironically, the most success that I had was with the limited and much maligned iOS Voice Control that showed up in iOS 3. As much as I heard and read people’s complaints of it, Voice Control actually worked very well for me, even while driving. I have always had my contacts sorted and displayed last name first, so once I figured out that I needed to speak them in that same format to start a call, Voice Control was very reliable.

So, since apps weren’t integrated enough with the OS to make for a seamless experience, I went a different direction- Services. I tried both Jott and ReQall’s subscription voice services at different times over the past four years, and at times, the relationship was very smooth. Since these services work over a phone call phone, using voice commands and dictating with a Bluetooth headset were much smoother experiences. Also, thanks to their tie-ins with other services like Google Calendar and Toodledo, both of which I have used, it was easy to set tasks and reminders that would end up on my device. Also, since I uploaded my contacts to each service at different times, I was also able to dictate emails and text messages to anyone with ease. Well, ease for four years ago, at least. And at a significant monthly or yearly cost.

Unfortunately, while Jott was the better of the two services, it died a slow death over the last few years. Ironicaly, Dragon, who provides the voice recognition for iOS’s Siri service, actually bought Jott a while back. Many users, like myself, thought this would mean more capital for Jott to improve and expand their service, but that was not the case. Dragon basically let Jott wither and languish, and then completely killed it off. Who knows, maybe some of their tech has been integrated into what we are using every day in Siri?

So, while services were a better experience for me than apps, the cost and the ultimate death of Jott ultimately brought that experiment to an unsuccessful end. So, I’ve been going without on the road over the last year. Dragon Dictation wasn’t worth the effort, especially while driving, and ReQall wasn’t worth the price. This has been a real drag for me, because I often spend two or more hours driving at a time, and I tend to think of and plan out a lot of my tasks and schedule during this time. This leaves me to remember them and get them down when I stop the car. However, I’m also sort of scatterbrained and forgetful, which is a bit of a problem. In fact, that’s one of the major reasons I got into using digital organizers and PDAs several years ago. What’s the point of using a device if it doesn’t help you when you need it? (Note to any Android fanboys who want to comment on this- I have owned two Android phones and, yes, the integrated voice control is very good. It’s just pretty much everything else that I dislike. Been there. Bad fit. It just isn’t an option for me.I just needed a great voice option to complete my iOS experience.)

So, you know my past frustrations. So, how is Siri stacking up, you ask? So far, I absolutely love it. LOVE IT! In fact, it has worked so well for me, that I have changed up some of the services I use and ways I do things so that I can take better advantage of its capabilities while on the road. For example, I have been using Pocket Informant on iOS for over two years now. While Apple added the ability to use Google Calendar natively, I have always used PI’s direct Google sync because it offered some additional functionality and flexibility. However, by going through PI, I wouldn’t be able to use Siri, and if I tried to use both native Google sync and PI simultaneously, I would have ended up with everything duplicated.

I had already been meaning to dump Google Calendar (and other Google services, for other reasons that you can read about here) and go back to Exchange for work stuff and iCloud for personal use for a while now. I’ve just been so busy at work lately that I didn’t want to take the time to re-assign all of my appointments. After a week with Siri, though, I went ahead and made time this last weekend, and I’m glad that I did. Now I can add appointments with my voice with ease, and not have to worry about where they will end up, or if I can see them everywhere I need to.

Thankfully, the rest of my habits already lined up pretty well with Siri. I have used Toodledo for my work task management and Evernote for job notes for years now, as well.  Since both can accept new tasks and notes via email, it is easy to use Siri to enter new content without changing things up too much. This does require a little triage after the fact to assign things like projects, folders, and such, but just getting the idea out of my head and recorded is what I’m concerned with, and Siri does a great job with this.

I have also found that, even though I will still use Toodledo for work project management and Evernote for the bulk of my work notes, I am using the native Reminders and Notes apps a lot more than I used to. Both are out of their dusty old folders, and back on my first home screen. Since they are both synced with iCloud, I no longer have to worry about my data getting land locked on my device. Also, the ease with which Siri can fully interact with those apps is a BIG plus, especially with the Reminders app. I now use it for all of my shopping lists, and basic personal tasks, leaving Toodledo for work project management.

So, I’ve talked a TON about my experience pre and post-Siri. How about some practical tips for using Siri on the go? In this article, I am going to focus on using Siri with a Bluetooth headset. Anyone who has used Siri by holding the iPhone up to their head knows that it works flawlessly using this method. It also works very, very well with Apple’s included headset with mic. Things can be a little different, however, when you bring a 3rd party device to the table. But, if you dock your iPhone in the car like I do, and have it connected to your car’s stereo, you need Siri to work well without the wires and away from your face.

I started testing this out on a work trip last week and found that, when it comes to Bluetooth headsets, you really do get what you pay for. I have had a reliable Plantronics 510 for three years now, and while the voice call quality and battery life are still acceptable, the mic just doesn’t cut it for Siri. Not even close. Voice Dialing works well, like it always has, but the dictation was bad. REALLY bad. I was pretty worried, because I was really looking forward to using Siri to dictate not just appointments and tasks, but also ideas, or even parts of reviews while on the go. Headset one was a big swing and a miss.

I actually have two Bluetooth headsets, the second being a Samsung WEP870 with a stereo lanyard that I use for listening to tunes wirelessly. Unfortunately, the audio quality of this headset is even worse than my Plantronics, so I really didn’t expect too much. I tried it anyway, and it lived down to my expectations. So, I was left with the wired headset, which works well, but doesn’t fit with the way I use the device in the car. That was not going to be an acceptable long term solution for me.

I know better than to just give up, though. Since my Plantronics is three years old, I figured it was time to replace it anyway, so it was time to head to the store. I ended up finding a Jawbone Icon headset on clearance at Radio Shack for $68.64. They have a great reputation for quality audio and noise cancellation, and the price seemed very reasonable for a brick and mortar store. It was worth every penny. The experience and consistency with Siri are daylight and dark from my first two tests. In a quiet room, the Icon is nearly letter perfect (well, at least perfect at what I am saying or mumbling, which isn’t always correct). In a car with road noise, the performance isn’t much worse, and that makes Siri the powerful mobile experience it should be. I can use it the way that I want, any time I need it. It always works, even with my iPhone in a dock and plugged into my stereo.

There have been a couple of minor annoyances with this setup. If you have the Icon’s A2DP turned on and trigger Siri, whatever you were listening to on your car stereo before will be routed to the headset after you are done. You can tap the audio source icon on the iPhone’s screen to switch it back, but that requires taking some attention off of the road. However, thanks to the fact that Jawbone offers a web interface to set up your Icon headset when it is plugged into a computer via USB, you can change a variety of settings without messing with any buttons or switches on the device. This includes being able to turn off A2DP, which solved this problem for me. Since the Icon isn’t a stereo headset, this isn’t a big deal to me.

Another advantage of this feature, is that the software and features of the Icon can be updated to take advantage of new phones, or patch incompatibilities. From some of the reviews I have read, Jawbone has been pretty proactive in this department, so I wouldn’t be shocked to see some Siri customization in a future update.

Another minor annoyance is that occasionally, when you trigger Siri by holding the Icon’s action button for the first time in a while, the delay for the headset to fully connect is long enough that Siri times out waiting for your command. However, the Siri icon remains on the screen, so it is easy to just tap it to proceed. You can also just press the Icon’s action button again, which will instantly connect the second time. It doesn’t do this all of the time, but it is annoying. Hopefully jawbone can address this with an update in the future. All in all, despite these minor issues, I would highly recommend this headset for the iOS user who wants to take full advantage of Siri on the road.

So, to sum it up, Siri works like a dream on the road, even while driving, as long as you are using it the right way. If you don’t use your iPhone to play music in the car, and either hold it to your ear or use the wired headset for calls, then you are already set. Siri should work very well, and with a high degree of accuracy. If you use a Bluetooth headset, especially a lower end, lower cost device, you may need to re-think your equipment if you want to use Siri wirelessly. For me, getting to use Siri to digitally transmit the stuff floating around in my forgetful and disorganized mind to my iPhone in a safe and easy way while driving, was worth every penny. If your headset doesn’t work so well in the car, just bear in mind that other headsets out there DO perform well. It’s just a matter of money and value to the individual user.

So, since I hit a home run with the Jawbone Icon the first time out, I haven’t tried any more new Bluetooth headsets with Siri. If any of you have found a Bluetooth headset, or even a handsfree speaker that works well with Siri, please let everyone know in the comments. For any of you who have cars with built-in Bluetooth systems that connect to the iPhone, I would love to hear about your Siri experiences, as well. Also, if you have Bluetooth equipment that doesn’t work well, that would definitely be valuable information, as well.

Before parting, here are a few extra tips for using Siri on the road:

  • Speak slightly slower, and a little louder than normal. Don’t over exaggerate, because Siri learns your speech patterns over time, and if you deviate too much, your accuracy will take a big hit.
  • Be sure to clearly enunciate your words, especially ending consonant sounds.
  • Make sure that whatever Bluetooth headset you are using, it is pointed toward your mouth, and seated properly.
  • If possible, mount the phone where you can easily touch the screen while keeping your focus on the road. Fortunately, the Siri button and screen prompts for appointments, reminders, notes, etc, are large enough that you don’t have to aim carefully to tap them.
  • If your headset doesn’t have the best reception distance, make sure it has clear line of sight to your phone. This usually isn’t an issue in the car.
  • When requesting that Siri look up information, be as accurate and detailed as you can.  Also remember that the contexts and relationships that it has established for you and others are also important. If Siri doesn’t recognize your request, try wording it slightly differently.
  • Despite my earlier comment about speaking your contact names last name first with Voice Control, Siri actually seems to work better with first name, then last name in my limited experience.
  • Like Voice Control, Siri does not recognize Company Name contacts that don’t have any other name elements set up. If you want to have a generic contact entry for Acme Products, for example, set up a Nickname under the contact with what you want to speak to have the number called. Then, Siri will recognize it, even though there is no first or last name set up.
  • Limit extraneous noise in the car as much as you can. In other words, don’t try to use Siri over others talking in the car or over the radio. No headset will pull that off in tight quarters, not even my new Jawbone. Try holding your iPhone to your head if you have to use it in a crowded vehicle.
  • If you have kids in the car, especially adolescent to teenage kids,  good luck with that. You may be wasting your time trying to escape their intentional interference.

Also, bear in mind that there are things Siri won’t do, at least not yet:

  • If you use multiple calendars like I do, Appointments and Meeting can only be created in your default Calendar. Siri will, however, recognize events in those Calendars if you request that it read appointment or meeting information to you.
  • You cannot specify reminder times for Calendar events. If you have a default reminder time set in the iOS settings, it will be used.
  • You can cancel the sending of an email or text message, or the creation of an appointment or task, but Siri will not delete things once they have been created.
  • Siri cannot open 3rd Party apps and does not directly integrate with any at this time.
  • Siri cannot tweet directly, even though Twitter has been directly integrated into iOS 5. If I had to guess, this will probably be available before the next major iOS update. However, you can use text messages to send tweets once you set the feature up with your Twitter account.
  • When you initiate dictation via the keyboard icon, you also have to tap the large mic button again when you are finished. Dictation will not end automatically when you stop speaking. This is a curious ommition, since the Dragon Dictation app does have this capability.

If you are looking for more helpful hits on using Siri to the fullest, no matter where you are, check out Talking to Siri: Learning the Language of Apple’s Intelligent Assistant by Steve Sande and Erica Sadun, which sells for $4.99 on Amazon, and works with the free Kindle app. I own this book, and it is extremely useful, especially in learning all of the ins and outs punctuation, spelling, capitalization, and other fine points and details of dictation.

Since iOS On The Road will be an ongoing series, I would love to get some ideas for future articles that you, our loyal and insightful readers, would be interested in. I have several things in mind, but I definitely want to know what you want insight on, as well. Feel free to hit me up with ideas here in the comments, or at my Twitter account, @jhrogersii. I look forward to hearing from you. Now, if you will excuse me, it’s time to get back on the road.


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  • Shilo

    What a great feature, thanks, I look forward to further articles. I also have an iPhone 4S and last weekend installed the Belkin Bluetooth Car Handsfree Kit (Amazon, about $70). So far I’m loving it. Works well with Siri, and uses the car stereo for the music on my iPhone. It requires an AUX input for your car stereo but if your car has one, installation is a no-brainer. Microphone/Activation button attaches to the dash; power comes from a cigarette lighter plug (into which you can plug your phone charging USB cable if you wish)…it’s exactly what I had been looking for to take advantage of the music on my phone without having to use an earpiece. Don’t know if I’m allowed to post the Amazon link, but I’ll try: http://www.amazon.com/Belkin-Bluetooth-Hands-Free-Blackberry-Smartphones/dp/B004CLYJ2I/ref=pd_sim_cps_1

    • jhrogersii

      Thanks for reading, Shilo, and especially for the handsfree recommendation.

  • John in SF

    I’m a cab driver and find Siri very useful. I also have a Jawbone Icon. The problem I have is during conversations with Siri, sometimes it won’t recognize my responses. That is, if it asks me for confirmation or clarification, it does not always register my answer through the headset. I have to turn the Icon off and talk directly into the iPhone for it to hear me.

  • jhrogersii

    Hello John in SF. I’m sorry to hear about your issues with the Icon. I tried duplicating this with my headset, but did not have this problem. However, I have the latest software updates loaded on mine. Have you tried using Jawbone’s setup website, MyTalk? If not, here is the link:


    If you haven’t used it before, you will need to create an account first. Then, after you connect your headset, MyTalk will prompt you to download a piece of software that the website uses to connect to the Icon via the USB cable. Once the website can recognize it, it will tell you if there are any updates for your headset. Loading the latest software should fix your problem. I actually updated mine before I paired it with my iPhone, so I am not sure how it operated with the original software.

    If this doesn’t work, it may time for a call to Jawbone, but feel free to let me know if you have any more trouble, as well. Good luck, and I hope this makes Siri an even better experience for you.

    • Tim

      I have a jawbone icon as well and love it except for the fact that it will not initiate Siri. When I press and hold the action button for the 2 seconds that the directions say I hear 1 beep then when I let go of the action button I hear a dull beep and then nothing happens. Am I missing something? I have the latest software and everything is up to date but it’s kind of frustrating. Any help is greatly appreciated. Thank you.

      • jhrogersii

        That’s wierd. Mine says “Voice Dialing,” and then pulls up Siri. Have you gone to the web interface tool and set the button action to voice dialing?

  • Paul in Albany

    Great advice! I’ve never used a Bluetooth headset, but am hoping it will help me make better use of Siri. Can you tell me which model Jawbone Icon you are using? I looked the Icon up on Amazon, and there are several different models. Thanks –

  • Rob

    Bummer. I have the same Belkin, and it’s no where close to as good as speaking to the phone. I’ve quit trying to use it. I’m a big fan of Siri when I can have my attention on the phone, but it was my search for a headset solution that led me to this page. Ironic that the second suggestion I see is the very one that won’t work for me!

  • Mat

    I have had less than 50% recognition with Siri on my Jawbone ICON. However, this was back around the end of November. I’ll check again for updates, but below is the response I received from Jawbone after asking them about Siri support. (They said that they don’t current support Siri).

    Response Via Email(Juan) – 11/28/2011 05:00 PM
    Hi ,

    Thank you for contacting us and we do apologize for the difficulties that you are experiencing. The Jawbone Is not compatible with the iphone siri at this moment . we are working for a mytalk update for you guys soon. When we have some information on this topic you will receive an email about the new up date. If you have any other questions give us a call 1-877-254-7426 with your reference number 111125-000007.


    The Jawbone Support Team
    1-877-ALIPHCO (1-877-254-7426)
    Weekdays 6AM-7PM (Pacific)

    • jhrogersii

      I’m sorry to hear you are having issues. I’m curious. How and where do you tend to use Siri with your Jawbone? Mine is mostly in the car and in quiet environments. I have noticed that my success rate with dictation goes down quite a bit when it is raining or extremely windy out. Also, I have had issues the few times I have attempted it in loud rooms.

      That is my experience with dictation. However, I rarely have any issues getting Siri to make calls or set up appointments correctly. It is hit and miss with proper names or special phrases, but it does that no matter if you use a headset or not.

      I can say that on a handful of occasions I have had a really tough time getting Siri to do anything right. In each instance, turning the Icon off and back on, which forces a new Bluetooth connection, has fixed the problem for me.

      It doesn’t surprise me at all that Jawbone states that they aren’t compatible with Siri, since it isn’t their product and they have no control over it. However, it would be nice to get an update down the line that will enhance the experience.

  • Gav

    Well here is an update about hands free while driving. I love the iPhone 4S awesome apps etc, but crap for handsfree. I use the Jawbone Icon or Noise Assasin with say the Nokia Lumia series and it is extremely clear and accurate. Eg, text message comes in and it asks you if you want it read and then allows you to respond, call or finish… all with 95% accuracy.

    The iPhone’s SIRI does not seem to work through the bluetooth feature, only directly into the phone or wired headset 🙁

    Test it, more than 1m away and it’s useless on iPhone with SIRI and even if it does work 40% it takes forever , the Lumia is clean accurate and fast, like within 2 seconds 🙂

  • jhrogersii

    Thanks for responding, Gav. I honestly haven’t tried the my Icon with a Windows Phone, so I can’t comment on that. However, I’m still seeing solid performance from Siri with my headset. In fact, it has been a relief re-gaining access to Siri this week, as I was locked out due to some kind of bug in the last iOS 6 beta that a simple reset or Network Reset wouldn’t fix. I got it back with Beta 4 on Monday, and have been much happier in the car since.

    Have you tried upgrading your Icon or checking the profile using Jawbone’s website interface? I only say this because there have been a few updates related to voice dialing in general, and Siri specifically, that they have addressed. I also know that the profile I last loaded a few months ago mentioned Siri in the description.

    I know these changes have had some positive effects. When I first started using the Icon just before I wrote this article, there were occasions when I would initiate Siri by holding the Icon’s button, and the delay between this and the full audio connection to the headset would be too long, and Siri would time out and stop listening. This no longer happens to me since the last update. Any time I start Siri with the headset now, it works for me.

    Sorry you are having issues, but if you haven’t updated, you should. It could make a big difference in the performance you are seeing.