diff --git a/.github/actions/spelling/patterns/patterns.txt b/.github/actions/spelling/patterns/patterns.txt
index 47f902f90..2e89f5e25 100644
--- a/.github/actions/spelling/patterns/patterns.txt
+++ b/.github/actions/spelling/patterns/patterns.txt
@@ -4,7 +4,7 @@ https://www\.itscj\.ipsj\.or\.jp/iso-ir/[-0-9]+\.pdf
 https://www\.vt100\.net/docs/[-a-zA-Z0-9#_\/.]*
 https://www.w3.org/[-a-zA-Z0-9?&=\/_#]*
 https://(?:(?:www\.|)youtube\.com|youtu.be)/[-a-zA-Z0-9?&=]*
-https://(?:[a-z-]+\.|)github(?:usercontent|)\.com/[-a-zA-Z0-9?%&=_\/.]*
+https://(?:[a-z-]+\.|)github(?:usercontent|)\.com/[-a-zA-Z0-9?%&=_\/.+]*
 https://www.xfree86.org/[-a-zA-Z0-9?&=\/_#]*
 [Pp]ublicKeyToken="?[0-9a-fA-F]{16}"?
 (?:[{"]|UniqueIdentifier>)[0-9a-fA-F]{8}-(?:[0-9a-fA-F]{4}-){3}[0-9a-fA-F]{12}(?:[}"]|</UniqueIdentifier)
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index da6f3a476..5a3860bf7 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -99,15 +99,29 @@ If you don't have any additional info/context to add but would like to indicate
 
 ## Contributing fixes / features
 
-For those able & willing to help fix issues and/or implement features ...
+If you're able & willing to help fix issues and/or implement features, we'd love your contribution!
+
+The best place to start is the list of ["Easy Starter"](https://github.com/microsoft/terminal/issues?q=is%3Aopen+is%3Aissue+label%3A%22Help+Wanted%22+label%3A%22Easy+Starter%22+) issues. These are bugs or tasks that we on the team believe would be easier to implement for someone without any prior experience in the codebase. Once you're feeling more comfortable in the codebase, feel free to just use the ["Help Wanted"](https://github.com/microsoft/terminal/issues?q=is%3Aopen+is%3Aissue+label%3A%22Help+Wanted%22+) label, or just find an issue your interested in and hop in!
+
+Generally, we categorize issues in the following way, which is largely derived from our old internal work tracking system:
+* ["Bugs"](https://github.com/microsoft/terminal/issues?q=is%3Aopen+is%3Aissue+label%3A%22Issue-Bug%22+) are parts of the Terminal & Console that are not quite working the right way. There's code to already support some scenario, but it's not quite working right. Fixing these is generally a matter of debugging the broken functionality and fixing the wrong code.
+* ["Tasks"](https://github.com/microsoft/terminal/issues?q=is%3Aopen+is%3Aissue+label%3A%22Issue-Task%22+) are usually new pieces of functionality that aren't yet implemented for the Terminal/Console. These are usually smaller features, which we believe
+  - could be a single, atomic PR
+  - Don't require much design consideration, or we've already written the spec for the larger feature they belong to.
+* ["Features"](https://github.com/microsoft/terminal/issues?q=is%3Aopen+is%3Aissue+label%3A%22Issue-Feature%22+) are larger pieces of new functionality. These are usually things we believe would require larger discussion of how they should be implemented, or they'll require some complicated new settings. They might just be features that are composed of many individual tasks. Often times, with features, we like to have a spec written before development work is started, to make sure we're all on the same page (see below).
+
+Bugs and tasks are obviously the easiest to get started with, but don't feel afraid of features either! We've had some community members contribute some amazing "feature"-level work to the Terminal (albeit, with lots of discussion 😄).
+
+
+Often, we like to assign issues that generally belong to somebody's area of expertise to the team member that owns that area. This doesn't mean the community can't jump in -- they should reach out and have a chat with the assignee to see if it'd okay to take. If an issue's been assigned more than a month ago, there's a good chance it's fair game to try yourself.
 
 ### To Spec or not to Spec
 
 Some issues/features may be quick and simple to describe and understand. For such scenarios, once a team member has agreed with your approach, skip ahead to the section headed "Fork, Branch, and Create your PR", below.
 
-Small issues that do not require a spec will be labelled Issue-Bug or Issue-Task.
+Small issues that do not require a spec will be labelled `Issue-Bug` or `Issue-Task`.
 
-However, some issues/features will require careful thought & formal design before implementation. For these scenarios, we'll request that a spec is written and the associated issue will be labeled Issue-Feature.
+However, some issues/features will require careful thought & formal design before implementation. For these scenarios, we'll request that a spec is written and the associated issue will be labeled `Issue-Feature`. More often than not, we'll add such features to the ["Specification Tracker" project](https://github.com/microsoft/terminal/projects/1).
 
 Specs help collaborators discuss different approaches to solve a problem, describe how the feature will behave, how the feature will impact the user, what happens if something goes wrong, etc. Driving towards agreement in a spec, before any code is written, often results in simpler code, and less wasted effort in the long run.