diff --git a/.github/PULL_REQUEST_TEMPLATE.md b/.github/PULL_REQUEST_TEMPLATE.md
index 7745d97e52ddf..9f68b4fbc0156 100644
--- a/.github/PULL_REQUEST_TEMPLATE.md
+++ b/.github/PULL_REQUEST_TEMPLATE.md
@@ -1,4 +1,12 @@
 
 ----
 
+### All Submissions:
+
+* [ ] Have you followed the guidelines in our [Contributing guide?](../CONTRIBUTING.md)
+
+### Adding new Unconventional Dependencies:
+
+* [ ] This PR adds new unconventional dependencies following the process described [here](../CONTRIBUTING.md/#adding-new-unconventional-dependencies)
+
 *By submitting this pull request, I confirm that my contribution is made under the terms of the Apache-2.0 license*
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index ba1e2a49f5c97..8797024d1c1c6 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -292,6 +292,8 @@ $ yarn watch & # runs in the background
 
 * Shout out to collaborators.
 
+* Call out any new [unconventional dependencies](#adding-new-unconventional-dependencies) that are created as part of your PR.
+
 * If not obvious (i.e. from unit tests), describe how you verified that your change works.
 
 * If this PR includes breaking changes, they must be listed at the end in the following format
@@ -312,6 +314,30 @@ $ yarn watch & # runs in the background
 * Make sure to update the PR title/description if things change. The PR title/description are going to be used as the
   commit title/message and will appear in the CHANGELOG, so maintain them all the way throughout the process.
 
+#### Adding new unconventional dependencies
+
+**For the aws-cdk an unconventional dependency is defined as any dependency that is not managed via the module's
+`package.json` file.**
+
+Sometimes constructs introduce new unconventional dependencies.  Any new unconventional dependency that is introduced needs to have
+an auto upgrade process in place. The recommended way to update dependencies is through [dependabot](https://docs.github.com/en/code-security/supply-chain-security/keeping-your-dependencies-updated-automatically/configuration-options-for-dependency-updates). 
+You can find the dependabot config file [here](./.github/dependabot.yml).
+
+An example of this is the [@aws-cdk/lambda-layer-awscli](packages/@aws-cdk/lambda-layer-awscli) module.
+This module creates a lambda layer that bundles the AWS CLI. This is considered an unconventional
+dependency because the AWS CLI is bundled into the CDK as part of the build, and the version
+of the AWS CLI that is bundled is not managed by the `package.json` file. 
+
+In order to automatically update the version of the AWS CLI, a custom build process was
+created that takes upgrades into consideration. You can take a look at the files in
+[packages/@aws-cdk/lambda-layer-awscli/layer](packages/@aws-cdk/lambda-layer-awscli/layer)
+to see how the build works, but at a high level a [requirements.txt](packages/@aws-cdk/lambda-layer-awscli/layer/requirements.txt)
+file was created to manage the version. This file was then added to [dependabot.yml](https://github.com/aws/aws-cdk/blob/ab57eb6d1ed69b40ed6ec774853c275785acace8/.github/dependabot.yml#L14-L20)
+so that dependabot will automatically upgrade the version as new versions are released.
+
+**If you think your PR introduces a new unconventional dependency, make sure to call it
+out in the description so that we can discuss the best way to manage that dependency.**
+
 ### Step 5: Merge
 
 * Make sure your PR builds successfully (we have CodeBuild setup to automatically build all PRs).
@@ -343,6 +369,7 @@ Breaking changes come in two flavors:
 * API surface changes
 * Behavior changes
 
+
 ### API surface changes
 
 This encompasses any changes that affect the shape of the API. Changes that