Getting Started

There are a handful of things you need to do to get up and running with Gertrude. This tutorial is meant to walk you through the required steps, and also to give you a bit of practice using all of the core features of Gertrude.

NOTE: If you'd prefer to watch a step-by-step video showing all aspects of getting started with Gertrude, click here.

Setting up your parent account

To start out, if you haven't already created a Gertrude account you'll need to do that first. To create an account click this link and follow the sign-up instructions. No credit card is required, the first 60 days are totally free, and you can cancel at any time.

Adding your first child

Once you have your Gertrude account created you'll need to start by adding at least one child. A "child" in Gertrude represents someone that you want to protect. This is very often one of your own children if you are a parent using Gertrude to protect your kids—but it could also be a peer whom you are protecting in a relationship of accountability. You'll need to add at least one child to do anything useful with Gertrude.

To add a child, click the link in the dashboard of the Gertrude parents website, or select "children" from the side bar on the left hand and click the button to add a new child.

Go to the 'Children' screen to add your first child

Enter the child's name, and click to save the new child.

Enter your child's name, and click 'save'

Mac App Connection Code

To finish setting up your first child, we'll need to install the Gertrude Mac app on their computer. But before we do that, you'll grab a one-time connection code to connect the app to the child you just added. To do so, click the Add a computer" button on the edit child screen. You'll see a pop-up giving you a special one-time connection code. Write this code down somewhere; you'll be using it shortly.

Click Get connection code

Then copy down the code

Connecting a computer

For the next part of the process you'll need to switch over to the computer that will be used by the child you're protecting. You might already be using that computer. But if you're a parent working through this tutorial on your own computer and your child uses a different computer you'll need that computer in front of you to do the next few steps of initial setup.

Downloading the Gertrude macOS app

On the computer that will be protected, login to the macOS user that you desire to protect, then open a web browser, visit the Gertrude website download page, and click the download link to download a copy of the most recent version of the Gertrude macOS app. Double-click on the downloaded file and then drag the Gertrude application into the applications folder.

Drag the Gertrude app into Applications

Next, double-click on the Gertrude application icon in the applications folder to launch it for the first time. Once Gertrude is launched, the only visible difference you'll see is that there will be a new icon in your menu bar, as shown below:

The Gertrude app menu bar icon in the upper right corner

The first time you click this icon, Gertrude will prompt you to enter a connection code. Enter the connection code that you wrote down earlier. When you submit the code you should receive a confirmation that the Gertrude Mac app is successfully connected.

Click Connect to child

And enter the connection code you got from the parents websitk

Enabling the internet filter

The next thing you need to do is to turn on Gertrude's internet filter. Getting the filter fully activated takes a couple of steps, because the operating system wants to make very clear to you that Gertrude has your permission to filter all the internet traffic on this computer. To begin the process of starting the filter, click the Gertrude icon again and then click the "Turn on" button as shown below:

Click 'Turn on' to begin the process of enabling the filter

At this point, the macOS operating system will block Gertrude from installing a system extension. Click the button labeled "Open Security Preferences", or manually open up the System Preferences app, and choose "Security & Privacy" > "General".

Click 'Open Security Preferences'

From the "Security & Privacy" > "General". screen, click the unlock icon to authorize, and then choose to allow the system extension from Gertrude.

Allow Gertrude to install a system extension

As a final step, you should now see a prompt asking you if Gertrude can filter network activity.

Allow Gertrude to filter network content

Congratulations! Those steps are out of the way, and Gertrude has installed it's network filter. You won't have to repeat those steps again. If you click the Gertrude menu bar icon now, you should see that the filter is enabled.

The filter is now enabled

Monitoring child activity

Now that you've got the Mac app installed on your child's computer, if you go back to the parents website and click to edit your child, you'll some new options have appeared:

monitoring options

Now might be a good time set up monitoring if you wish. Gertrude allows you to see everything your children have typed and also can take periodic screenshots of your child's screens for you to review later. You can always change these settings later, but we recommend enabling them for the greatest safety, and also because it will help you learn about all of Gertrude's features as you work through this tutorial.

Enable monitoring, at least as while working through this tutorial

Keychains & Keys

Keychains

Near the bottom of the same screen is a section that allows you to attach what we call "keychains" to your child. One of the main features of Gertrude is that it acts as an internet filter for your child's Mac computers. Gertrude's filter blocks the entire internet, only allowing access to the sites and apps you specifically designate as safe.

Keys

The way you unblock part of the internet for your child is by granting them what we call a "key". A key either a) "unlocks" a single website, or b) grants a single app access to the internet. These keys are organized into groups called "keychains", and it's here on the edit child screen that you have the ability to add keychains to your child.

adding a keychain from the 'Edit child' screen

Until you add at least one keychain your child will have no access to the internet whatsoever while Gertrude's filter is enabled.

Creating your first key

You haven't created any of your own keychains yet, so currently the only keychains you can attach to this new child are publicly available keychains. We'll talk more about those later, but for now let's practice by setting up your own keychain with a single key.

Creating a new keychain

Either click the "create keychain" button in the popup shown in the image above, or alternatively you can click over to the Keychains screen from the left-hand sidebar, as shown below:

adding a keychain from the 'Keychains' screen

Click the add keychain button, then give your keychain a name, and optionally a description. Once you've named your keychain click the "add a new key" button, and a screen will pop up allowing you to create a new key.

Give your new keychain a name, then click 'create'

Two types of keys

There are two types of keys. The first, which is the most common, we call a website key. It allows access to a specific web address. For example, if your child has a specific online educational course or program that they access through a web browser, you could add a website key granting them access to just that program's website.

The second type of key is an app key. These keys allow you to grant specific applications full access to the internet. For instance, you could create an app key that allows only the Zoom app to bypass Gertrude's filter and have complete access to the internet. You should only do this with apps that are narrowly focused and that you are sure are safe for your children to use.

Creating and attaching your first key

For the sake of this tutorial, start by creating a single website key. Enter the address of a website that you want your child to have access to, and leave the rest of the options unchanged. If you can't think of a website to unlock, enter how-to-type.com, as we'll use that example later in the tutorial. Click "Create key" to finish the process.

Create your first key

Now that you've got a key and a keychain, you need to do one more step: attach that keychain to your child. Go back to the children screen, click to edit the child you added earlier, and then click to add a keychain. Select the keychain you just created by its name and save the child.

On the 'Edit child' screen, add the keychain

Exploring the Gertrude app

Next, let's take a few moments to explore the Gertrude app. Click the Gertrude app icon in the menu bar once again. You should now see that the filter is on. Some of the options in the drop-down menu are meant for your child to interact with, with one exception. The item labeled administrate is only for you as the Gertrude account owner.

The main Gertrude menu dropdown

The admin health-check screen

Click the "administrate" link now, entering your admin user and password to authenticate. You will see the Gertrude health check screen. This screen is meant to give you a glanceable overview of the Gertrude app, and to help you troubleshoot and fix common configuration issues.

The admin-only 'Health check' screen.

Ideally, you should see all green checkmarks, although when you're first getting set up it's common to have a few issues that need to be addressed. Take a moment and review any items that are not green and resolve them.

Taking the filter for a spin

Next, I close the admin window and open up a web browser like Google Chrome or Safari or Firefox. If you try to visit an address on the internet, you will notice that the page does not load. That's because the filter is running and blocking the entire internet with the exception of the addresses that you have specifically unlocked. When Gertrude blocks something, you'll see an empty error page that looks something like this:

What you'll see when Gertrude blocks a webpage

Earlier in this tutorial we created a website key. Let's test it now. Try to visit the website you specified when creating your first key. You should notice that your web browser does allow that page to load. This shows you that Gertrude's internet filter is working properly, that is, blocking all internet request except those that you specifically allowed.

This page was allowed because of the key we created earlier.

Techniques for unlocking websites

It's great to know that the Gertrude filter is working, but you probably need many more websites unblocked in order for the computer to be usable. In this section we will go over to techniques to make it simpler and faster for you to accomplish this.

Public keychains

The first technique is taking advantage of previously created public keychains. As we mentioned above, keys in Gertrude are always grouped into keychains. There are several reasons for this, but probably the main one is that it allows clusters of related keys to be easily shared and re-used. As an example, the website Art of Problem Solving (AOPS) is a widely used online educational platform. In order for it to work properly on a computer protected by Gertrude, it requires a handful of keys to unlock the web addresses used by that platform. There are thousands of students enrolled in AOPS classes. So it would be a shame if every Gertrude account owner had to re-create the same set of keys to grant access to AOPS. Instead, Gertrude offers a public keychain containing just the keys to unblock apps, which many people can share.

Adding a public keychain

To see how this works, let's temporarily give the AOPS keychain to your child. Go back to the computer where you set up and created your Gertrude account. Navigate to the Children screen and select the child you recently added. Click to add a keychain, and then search through the bottom section which lists public keychains, until you find the one for AOPS. Choose that keychain and save the child.

Find and add the 'AOPS' public keychain to your child

At this point, if you go back to the computer that is being protected by the Gertrude Mac app, you should be able to navigate to artofproblemsolving.com and it should load properly. This demonstrates the power and flexibility of using and sharing keychains.

You may want to spend a few minutes browsing through the list of publicly available keychains, you may find that one or more of them is useful to you. You'll also notice that some of the keychains are focused on unlocking a specific website or website-based programs, while others are focused on granting access to specific, narrowly focused applications like email clients or video conferencing apps.

You can also organize your own keys into keychains, but there is no requirement that you do so. Technically every key must belong to a keychain, but if you want, you can put all of the keys you create onto a single keychain. You may however find that it makes sense to you to also group your own keys topically. If you have multiple kids this can make it easier to mix and match and share keychains without causing more work for yourself.

Unlock requests

Probably the most common way to unlock parts of the internet for your children is by responding to a child-initiated unlock request.

Move back to the computer (or switch to the macOS user) being protected by the Gertrude macOS app. Start by thinking of a website that your child needs access to that you currently don't have a key for. Try to visit that website in a web browser and you'll notice once again that it is blocked: Gertrude's filter is not allowing access to that website, because there is no key instructing it to.

Click the Gertrude app icon in the menu bar and select the item entitled View network requests.

Click the 'View network requests...' option

This brings up a window whjch shows you a live display of all the requests that the Gertrude filter is handling and blocking.

The network requests window

With the network requests Gertrude window open, refresh the blocked page in your web browser. You should see one or more new blocked requests flowing in to the Gertrude window.

Lots of stuff in the network window is normal.

Assuming we can find the right request (more on that in a moment), the Gertrude app allows us to then send an unlock request to have that specific website unblocked. Once you get used to this, it's common that this method becomes the primary way in which you create new keys for your children.

The unlock request flow

1. A child tries to access a website on the internet, and are blocked.
2. They open the network requests window, and find the request that was blocked.
3. They then send an unlock request to you requesting that that website be unlocked.
4. Then you have the opportunity to review and approve or reject that request. You approve the unlock request by creating a key that unblocks that web address.

We'll walk through all four steps now, and we have a more detailed article with advanced tips and tricks on unlocking that you can refer to later, if necessary. Start by 1) clearing the requests to help you focus and find the correct request, then 2) click to filter by the partial word khan as shown below:

Clear the screen, then filter by 'khan'

Next, try the page again, by hitting the refresh button in your browser. This should trigger another block, but this time we're ready for it, we've cleared away the noise and are filtering for blocks containing khan. You should see something like this:

Huzzah! We found the blocked request!

To submit an unlock request for the block, click the small unlock icon, optionally add a comment, and then click submit.

Click the blocked request, then send.

Accepting an unlock request

Now that the unlock request is submitted, put back on your parent hat (you've been impersonating your child for the last few minutes), and visit the home screen of the parents website. You'll notice that there is a new unlock request visible:

The recently submitted unlock request in your parents website

Click to accept the request, and you'll be taken to a screen where Gertrude recommends a key that will unlock the given request. You're free to stop and edit the key if you want, but for now, just click to "Select keychain":

You can review and modify the key that will unlock the request

You next get to choose which keychain the key should belong to—you only have one keychain, so select it and click submit.

Select a keychain, and submit.

Back on the computer running the Gertrude macOS app, you should see a notification that the unlock request was accepted.

Back on the child's Mac, a notification that it was accepted.

And if you refresh the web page, you'll now have access to the previously blocked site.

Success! The site is now unblocked.

You should spend a few minutes with each of your children, showing them how to identify blocked requests and send unlock requests. In our experience, kids of all ages pick it up pretty fast. Once you're in a groove, your children will send you unlock requests when they need something, and you'll be notified via email, text, or Slack, and can approve or reject from your own computer or phone, no matter where you are.

Filter suspensions

There are times when, for a short period of time, it's convenient to disable Gertrude's filter completely. Examples of these sorts of situations include when your child is taking an online test, or doing some unusual activity or research. In these cases it doesn't make sense to go through the work of creating keys or unlock requests because the websites they will be visiting won't be needed again. For times like this, you as the parent have the ability to remotely suspend the filter for a designated period of time, after which it will resume normal filtering.

The suspend filter request flow

The way filter suspensions work is similar (although simpler) than unlock requests.

1. one of your children submits a "suspend filter request" from the Gertrude macOS app.
2. you (the parent) receive a notification via text message, email, or Slack
3. the link in the notification takes you to a screen where you can accept or deny

To request that the filter be disabled, the child begins by clicking the "Disable filter temporarily..." option in the Gertrude menu dropdown.

Click to request a filter suspension

The child is shown a form where they can fill out the length of time they wish to have the filter suspended, and optionally a comment explaining why the filter suspension is being requested.

The child picks a duration, and can add a comment

Once submitted (provided you've configured a notification in your settings screen), you'll receive an email, text or Slack letting you know that your child is requesting a filter suspension. You can grant or deny the request, and if desired, also change the amount of time requested.

You get to grant or deny the request, and modify the duration

Reviewing child activity

If you elected to enable monitoring of your child, you will be able to review your child's activity from within the Gertrude parents website. If you enabled key logging and screenshots as recommended in the beginning of this tutorial as recommended, you should already have a few items that you can review. To see how this works, login to the Gertrude parents website and go to the children screen and select the activity link from the child you added.

Go to 'Children' and click 'Activity'

You should see on the next screen that there are some unreviewed activity items. Click to view these and you will see a mixture of screenshots and text that was typed by the child.

Click to review activity

Activity items are a mix of screenshots and keystrokes (if both enabled)

Approving an item is essentially the same thing as deleting it. The idea is that an "approved" item does not need to be seen again. It's rare that you'll actually approve items individually—you'll notice when you have large amounts of items to review, that Gertrude gives you the option to approve them in chunks of one hundred at a time, and also you can approve an entire day at once at the bottom of the screen.