diff --git a/.spellcheck-en-custom.txt b/.spellcheck-en-custom.txt
index 385f076..97145be 100644
--- a/.spellcheck-en-custom.txt
+++ b/.spellcheck-en-custom.txt
@@ -45,6 +45,7 @@ DCO
 Dependabot
 dev
 disambiguating
+discoverability
 ditaa
 Docling
 docling
@@ -227,6 +228,7 @@ specifiying
 splitter
 src
 Srivastava
+SSL
 Staar
 Standup
 subcommand
diff --git a/docs/adr-custom-exceptions.md b/docs/adr-custom-exceptions.md
new file mode 100644
index 0000000..5f97a70
--- /dev/null
+++ b/docs/adr-custom-exceptions.md
@@ -0,0 +1,23 @@
+# InstructLab Custom Exceptions Pattern
+
+## Context
+
+The historically pervasive pattern for exception handling during application runtime is to catch internally raised exceptions in the CLI layer and use `click.secho` followed by `click.exceptions.Exit` to display a useful error message to the user before exiting the application. This leaves a risk of intermediate calls between the site of the exception and the user-facing layer changing, leading to missed new exceptions and outdated caught exceptions. A second issue is that of discoverability and verification: given a `click.exceptions.Exit` exception handling, it is not clear from the code where the caught exception originates from in the call stack, and, similarly, given a piece of code that can raise an exception, it is not clear from the local code whether that exception is properly handled in the CLI layer without investigation.
+
+These issues will compound whenever REST APIs begin development.
+
+## Decision
+
+InstructLab will adopt custom exceptions to handle specific faults which are then caught in the user-facing layer (CLI, REST API, &c).
+
+## Status
+
+Accepted
+
+## Consequences
+
+* Verification of exhaustive error handling will be clear within a code section that can raise.
+* CLI layer error handling will be easy to understand and trace.
+* Whenever REST APIs are developed, HTTP error codes should be easier to be associated with specific exceptions.
+* It should be easier to compose useful error messages for the user.
+* It should be easier to correctly scope exception handling (consider a `URLError` raised about SSL verification, for example, versus a custom `SSlVerificationException`).