Tracking Subscriptions

Subscriptions are increasingly common and show no signs of going away, regardless of what you may think about them.

With subscriptions being an important part of modern digital life, it seemed wise to find a way to keep track of them. First I turned to Bobby, which is an iPhone app that has been mentioned a few times on Mac Power Users for managing subscriptions.

Having used it quite a lot now, I can say that Bobby is both great and frustrating.

Bobby’s Best Bits

It’s great to be able to set the name, price, and “cycle” (usually monthly or annually) of a subscription. Bobby has a lot of services already built-in, which will show the appropriate logo and colors for the service. Once you have your subscriptions added in, you can see the average price you are paying on a weekly, monthly, or annual basis.

Perhaps the best feature is the ability to have Bobby remind you when a subscription is coming due. You can set it to remind you the same day (don’t do that, it might be too late to cancel), or 1-30 days/weeks/months/years before it’s due.

(Not sure that “years” is a necessary option. Does anyone have a subscription that they want to be reminded about a year before it expires/renews?)

I wish Bobby let me set a default reminder. Generally I want a week’s notice on all of my subscriptions, with a few exceptions (no need to tell me Netflix is renewing, thanks), but the default in Bobby is for no reminder, and the setting is not shown by default. (More on that below.)

We’ve all had the experience of getting an email saying “Thank you for renewing your annual subscription!” for a subscription that we had forgotten about and would have cancelled if we had remembered it. Bobby can help you avoid that, but you have to remember to add it each time.

Bobby also looks very nice. The fact of the matter is that most of us could very easily just create a spreadsheet with all of this information in it. But we don’t. (Ok, except for you in the back, frantically waving your hand. We see you, and we’re all very impressed. Now sit down.)

I much prefer to look at this:

My Subscriptions in Bobby

…than at some dry and boring spreadsheet. Until I used Bobby, all of my attempts at tracking subscriptions had been short-lived. Now I think that I’ll keep at it, using Bobby, despite some problems and frustrations.

It’s worth talking about those problems and frustrations, even though I don’t think any of them should stop you from using Bobby. If nothing else, you can learn from a few of my mistakes.

Bobby’s Bothersome Bits

Here’s the UI for entering a new subscription.

two Bobby screenshots, one showing ‘More Options’ expanded

(This particular screen is for adding a subscription for a service Bobby doesn’t know about, which is why it looks fairly plain. But I want to focus on the text and fields here anyway.)

On the left side is the default screen that you see whenever you are adding a new subscription. The blank space at the bottom is usually filled with the iPhone keyboard, which you’ll need for entering in the price, name, and (optionally) a description.

The right side is the same screen as the left, except that I have tapped on “More Options” to reveal, well, you know.

The fields for Color, First Bill, Cycle, Duration, Remind Me, and Currency are selected by tapping and choosing from various “pickers” rather than typing.

“First Bill” is not the same as “Next Renewal Date”

I made two mistakes with the “First Bill” field.

The first one was a minor edge case which I only discovered because I was using a Bluetooth keyboard with my iPhone: you can get to the “First Bill” field by pressing Tab and typing something like “2020-02-06” but the app will not recognize a date entered like that, so you need to tap on the field and choose the date from the date picker.

The second mistake was, in hindsight, both more obvious and more frustrating. The field quite clearly says first bill, but the dates that I entered were for the next renewal date. I did that mostly because those are the dates which are easiest to find. I have no idea when I first started using some of these services, and I mistakenly thought that what I should do was put in when I was going to have to pay for these services again.

That, as it turned out, was a significant mistake, because if the “first bill” date is in the future, then Bobby will not include the subscription amount in the monthly estimate until that date occurs.

So, for example, if I told Bobby that my “First Bill” for Dropbox was not until, say, October 15, 2020, then Bobby assumed I was not paying for Dropbox between now and then. Now, I don’t remember when I first started paying for Dropbox (it’s been several years), but what I should have done is put in “October 15, 2019” so Bobby would know that a) I am paying for it now and b) it will renew this year on October 15th.

At first, I found this baffling. Why would I want to track subscriptions unless I am paying for them? Are there people who make plans to start subscriptions at some point in the future?

The only subscription that I could see using this for was Apple TV+ which I have for free until November 2020 but then will renew at its usual price, but that is a rare exception.

Having thought about it further, I assume that this feature is intended to be used when you start a free trial. For example, if you sign up for a free one-week trial before you start paying, you could enter the subscription info into Bobby (along with a reminder, in case you want to cancel before the free trial ends).

Once you know how it works, it is easy enough to adjust. I went through and changed all “2020” to “2019” for any active subscriptions, and that seemed to get Bobby to understand that these were all active subscriptions.

Having said that, if I could change only one thing about Bobby, it would be to change “First Bill” to “Billing Date”. If I choose a date in the future, Bobby could ask me if I want to include the cost in my monthly subscription costs starting today. It seems like a solvable problem, but in the meantime, it’s easy to overcome once you know the system.


If I could change two things about Bobby, the second would be that I would not have “Cycle” hidden under “More Options”.

Maybe I’m unusual (don’t answer that) but most of my subscriptions are annual not monthly. In fact, in looking at my subscriptions, I have 10 which are monthly but 26 are annual. That’s a significant difference.1 The default “cycle” for subscriptions in Bobby is monthly which I can understand, since most subscriptions do have a monthly option. However, because the “Cycle” field was not shown by default, I made the mistake (several times) of setting annual subscriptions as monthly, which will really screw up the budget projections.

(Aside: If I could change two more things in Bobby, it would be a) let me set a default reminder for all new subscriptions and b) let me always see the “More Options” screen without having to tap to expand it every time.)

Again, here’s my list of subscriptions in Bobby:

This is a very visually pleasing screen, and you can see that Bobby has done very well identifying most of the subscriptions that I use.2 Under the amounts, you can see time-frames listed (6 months, 4 days, 3 weeks, etc.) which shows how long until that subscription comes up for renewal. That’s great, but I wish there was some indication of whether each subscription amount shown was per month, year, etc.

I’m not great as visual design, but I think it would be possible to put the subscription length after the price. So, for example:

Apple Music – $15.00

would become

Apple Music – $15/month


Dropbox – $120.00

would become

Dropbox – $120/year

You could even abbreviate “mon” for “month” and “yr” for “year” if needed. I would also drop .00 from prices. I tend to round-off all of my subscriptions anyway, because I’d rather see “$100” than “$99.99”. As I said, maybe I’m unusual.

My last frustration with Bobby is that there is no iPad app. I would love to see an iPad app, and ideally even a Mac app, because it would be so much easier to enter all of this information on my Mac where I could search my email for receipts/renewal information, and then enter it in Bobby.

Beyond Bobby

I really like Bobby and I’m glad that someone created an app like this. For $1 you can unlock unlimited subscriptions, but for $2 you can unlock all of its features and the developer will get a whopping $1.40 after Apple takes their cut.

That said, once I started tracking this information, I found a wanted a bit more. For example, for subscriptions outside of the App Store, I wanted to keep track of the URLs for changing or cancelling my subscription. I also wanted to know which payment method they were set up to use (I have a few subscriptions which are business expenses, so I want to make sure they have the correct credit card information.)

I also wanted to put any contact information that I had for the service, and if there’s one time when companies want to make sure you can contact them, it’s when you’re going to give them money, so subscription renewal emails are a good place to find contact info for each of these subscriptions.

Eventually, I did make that boring and ugly spreadsheet that I mentioned above, specifically so that I could add additional information.

Having it in a spreadsheet also means that I can see the data in other ways. For example, I made columns showing the monthly and annual price of each subscription. It’s one thing to know that I’m paying $18/month for YouTube, but when I realized that also meant I was paying $216/year for YouTube, it really brought home how expensive it is to hate commercials as much as I do.

As I mentioned, Bobby does have a reminder system built-in, but I still wish that I could see my subscriptions as a calendar in my calendar app.

I also found myself wanting to “group” subscriptions. For example, there are just some which I would never consider doing without; then there are some that I feel like I need to have even if I don’t love them (hello, Office 365); then there others that are support that I give mostly just because I want to (Six Colors, MacStories,, TidBITS, and Patreon).

Then there are weather apps. Until I compiled all of this info, I didn’t realize how many different weather apps I was paying for, ranging from $5/year to $25/year.

So when my subscription to forecast data through iStat Menus Weather came up for renewal, I realized that I could probably make do with one of the other weather apps that I was already paying for.

Pro-Tip: If you use iStat Menus via Setapp the weather data is included in your Setapp subscription price. I had bought iStat Menus before I started using Setapp, but now that I have Setapp, I decided installed iStat Menus through it, so I could keep using iStat Menus weather,. Setapp also includes Forecast Bar. I’m using them both. And Carrot Weather. Yes, I currently have 3 weather apps in my menu bar, and no, I don’t have a problem. What I do have is a forecast predicting up to 22" of snow.

This is harder than it sounds

What has amazed me is how difficult it actually is to track down all of my different subscriptions. I’ve been doing this for quite awhile and I still keep finding myself saying “Oh! I just thought of another one” including (literally as I was writing this) Setapp.

People used to criticize Apple for making it too hard to find your subscriptions list. It’s much easier now, just go to the app update screen on your iPhone or iPad and you’ll see it right near the top:

Screenshot of App Update screen

But the truth is that App Store subscriptions are easy to find and manage. It’s all of the other subscriptions that are harder to remember, but it’s worth taking the time to pay attention before you get another email thanking you for renewing a subscription that you had entirely forgotten about.

I thought I had a pretty good idea of how much I was paying in subscriptions, but seeing it all in one place surprised even me. It also got me to go ahead and cancel some of these that I no longer really need.

What I should do next is tally up the cost of my domain names. But… I really don’t wanna. A few years ago I had a terrible habit of collecting domain names, and they’re overly hard to let go. As I write that, I realize how stupid it is, but it’s true, and I suspect others can easily relate. Seeing those totalled would no doubt spur me to cut a few loose. After all, each domain name is probably worth about the same as a month of YouTube without commercials.

Update 2020-02-10

Someone on the Mac Power Users forum reminded me that David Sparks posted a Subscription Database (which is really a Numbers spreadsheet) that is set up to help you track subscription costs, and uses some spreadsheet calculations to do some of what I am doing by hand in my spreadsheet. Worth checking out.

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  1. I also have two subscriptions which are 24 months, one which is 36 months, and one which is 10 years. 150 points if anyone can guess what it is. 
  2. Bobby did not have an icon for Acorn, and when I added it, Bobby automatically chose the icon of a squirrel, which I thought was extremely clever. I realize that it was probably just random, but I like to think it wasn’t. Oh, one more item for the Bobby wishlist: let me use my own images, rather than just selecting from Bobby’s selection of icons. 

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