diff --git a/docs/Makefile b/docs/Makefile
index 3f658b555..eb03fe4c6 100644
--- a/docs/Makefile
+++ b/docs/Makefile
@@ -1,22 +1,36 @@
-.PHONY: buildimage build dev shell check
+.PHONY: buildimage build dev shell check genclidocs
+
+# 
+CORSO_BUILD_DIR := /tmp/.corsobuild
+CORSO_BUILD_CACHE := ${CORSO_BUILD_DIR}/cache
+CORSO_BUILD_MOD := ${CORSO_BUILD_DIR}/mod
+CORSO_BUILD_BIN := ${CORSO_BUILD_DIR}/bin
+
+CORSO_REPO := ${PWD}/..
+CORSO_REPO_CONTAINER := /go/src/github.com/alcionai/corso
+
+MDGEN_SRC_CONTAINER := ${CORSO_REPO_CONTAINER}/src/cmd/mdgen/mdgen.go
+MDGEN_BINARY := ${CORSO_BUILD_BIN}/mdgen
+CLI_DOCS_CONTAINER := ${CORSO_REPO_CONTAINER}/docs/docs/cli
+
 
 buildimage:
 	docker build -t "alcion/docs:latest" .
 
-dev:
+dev: genclidocs
 	docker run --rm -it \
 		-p 3000:3000 \
 		-v ${PWD}:/usr/src/docs alcion/docs
 
 VALE_TARGET ?= docs README.md
 
-dockercheck:
+dockercheck: genclidocs
 	docker run --rm \
 		-v ${PWD}:/usr/src/docs alcion/docs vale $(VALE_TARGET)
 	docker run --rm \
 	 	-v ${PWD}:/usr/src/docs alcion/docs markdownlint '**/*.md' --ignore styles/ --ignore src/ --ignore node_modules/
 
-check:
+check: genclidocs
 	vale $(VALE_TARGET)
 	markdownlint '**/*.md' --ignore styles/ --ignore src/ --ignore node_modules/
 
@@ -25,6 +39,25 @@ shell:
 		-p 3000:3000 \
 		-v ${PWD}:/usr/src/docs alcion/docs /bin/bash
 
-build:
+build: genclidocs
 	docker run --rm \
 		-v ${PWD}:/usr/src/docs alcion/docs npm run build
+
+genclidocs: ${MDGEN_BINARY}
+	@echo 'Auto-generating Corso CLI docs...'
+	docker run --rm -it \
+		-v ${CORSO_REPO}:${CORSO_REPO_CONTAINER} -v ${CORSO_BUILD_DIR}:${CORSO_BUILD_DIR} \
+		--workdir ${CORSO_REPO_CONTAINER}/src \
+		--entrypoint ${MDGEN_BINARY} \
+		golang:1.18 \
+		--cli-folder ${CLI_DOCS_CONTAINER}
+
+${MDGEN_BINARY}: ${CORSO_REPO}/src/** ${CORSO_REPO}/src/**/*.go
+	@echo 'Re-building Corso CLI docs auto-gen tooling...'
+	docker run --rm -it \
+		-v ${CORSO_REPO}:${CORSO_REPO_CONTAINER} -v ${CORSO_BUILD_DIR}:${CORSO_BUILD_DIR} \
+		--env GOCACHE=${CORSO_BUILD_CACHE} --env GOMODCACHE=${CORSO_BUILD_MOD} --env GOTMPDIR=${CORSO_BUILD_DIR} \
+		--workdir ${CORSO_REPO_CONTAINER}/src \
+		--entrypoint /usr/local/go/bin/go \
+		golang:1.18 \
+		build -o ${MDGEN_BINARY} ${MDGEN_SRC_CONTAINER}
diff --git a/docs/README.md b/docs/README.md
index 7c475d388..cac8b4ce2 100644
--- a/docs/README.md
+++ b/docs/README.md
@@ -24,6 +24,15 @@ make dev
 
 This command starts a local development server within the Docker container and will expose docs at [http://localhost:3000](http://localhost:3000).
 
+## Generating Corso CLI docs
+
+```bash
+make genclidocs
+```
+
+Corso's CLI documents are auto-generated. This command explicitly triggers generating these docs. This step will happen
+automatically for the other commands where this is relevant.
+
 ## Building static documentation
 
 ```bash