diff --git a/Makefile.build b/Makefile.build
index cbcec1393e..05be032c2f 100644
--- a/Makefile.build
+++ b/Makefile.build
@@ -24,24 +24,24 @@ define GIT_SHA
 endef
 endif
 
-ifndef DEBUG_KOTSADM
+ifeq ("$(DEBUG_KOTSADM)", "1")
 define LDFLAGS
 -ldflags "\
-	-s -w \
 	-X ${VERSION_PACKAGE}.version=${VERSION} \
 	-X ${VERSION_PACKAGE}.gitSHA=${GIT_SHA} \
 	-X ${VERSION_PACKAGE}.buildTime=${DATE} \
 "
 endef
+define GCFLAGS
+-gcflags="all=-N -l"
+endef
 else
 define LDFLAGS
 -ldflags "\
+	-s -w \
 	-X ${VERSION_PACKAGE}.version=${VERSION} \
 	-X ${VERSION_PACKAGE}.gitSHA=${GIT_SHA} \
 	-X ${VERSION_PACKAGE}.buildTime=${DATE} \
 "
 endef
-define GCFLAGS
--gcflags="all=-N -l"
-endef
 endif
diff --git a/hack/CONTRIBUTING.md b/hack/CONTRIBUTING.md
index 8f9bc3bff4..78e5a650d3 100644
--- a/hack/CONTRIBUTING.md
+++ b/hack/CONTRIBUTING.md
@@ -25,6 +25,12 @@ Next, you can build and run all server components in the Kubernetes cluster with
 skaffold dev
 ```
 
+To enable delve run:
+
+```
+DEBUG_KOTSADM=1 skaffold dev
+```
+
 ## Notes:
 - Go code will not be rebuilt automatically.  Run `make kotsadm` again to make the new binary and restart the pod.
 - After installing restic/velero, `kubectl -n velero edit daemonset restic` to change the volume hostPath mount from:
diff --git a/hack/dev/Dockerfile.skaffold b/hack/dev/Dockerfile.skaffold
index 86f91d8c40..b3b26cc155 100644
--- a/hack/dev/Dockerfile.skaffold
+++ b/hack/dev/Dockerfile.skaffold
@@ -12,9 +12,12 @@ COPY web/webcontent.go ./web/webcontent.go
 COPY web/dist ./web/dist
 COPY kotskinds ./kotskinds
 
-RUN DEBUG_KOTSADM="true" make kotsadm
+ARG DEBUG_KOTSADM=0
+
+RUN make kotsadm
 
 FROM debian:buster
+
 RUN apt-get update && apt-get install -y --no-install-recommends curl gnupg2 \
   && curl -k https://www.postgresql.org/media/keys/ACCC4CF8.asc | apt-key add - \
   && echo "deb http://apt.postgresql.org/pub/repos/apt/ buster-pgdg main" > /etc/apt/sources.list.d/PostgreSQL.list \
@@ -165,5 +168,10 @@ COPY --from=builder /go/src/github.com/replicatedhq/kots/bin/kotsadm .
 EXPOSE 40000
 
 # Should be entrypoint
-ENTRYPOINT [ "/dlv", "--listen=:40000", "--continue", "--headless=true", "--api-version=2", "--accept-multiclient", "exec"]
-CMD ["/kotsadm", "api"]
+
+ARG DEBUG_KOTSADM=0
+
+ENV DEBUG_KOTSADM=${DEBUG_KOTSADM}
+
+ADD hack/dev/entrypoint.sh .
+ENTRYPOINT [ "./entrypoint.sh"]
diff --git a/hack/dev/entrypoint.sh b/hack/dev/entrypoint.sh
new file mode 100755
index 0000000000..d739b07c6e
--- /dev/null
+++ b/hack/dev/entrypoint.sh
@@ -0,0 +1,7 @@
+#!/bin/bash
+
+if [ "$DEBUG_KOTSADM" = "1" ]; then
+    /dlv --listen=:40000 --continue --headless=true --api-version=2 --accept-multiclient exec /kotsadm api
+else
+    /kotsadm api
+fi
diff --git a/skaffold.yaml b/skaffold.yaml
index c9764ae0f6..8cc0cf9c75 100644
--- a/skaffold.yaml
+++ b/skaffold.yaml
@@ -9,9 +9,17 @@ profiles:
       kustomize:
         paths: 
           - "./kustomize/overlays/kotsstore"
+  - name: debug
+    activation:
+      - env: DEBUG_KOTSADM=1
+    patches:
+      - op: add
+        path: /build/artifacts/1/docker/buildArgs
+        value:
+          DEBUG_KOTSADM: 1
   - name: codespace
     activation:
-      - env: USER=codespace 
+      - env: USER=codespace
     build:
       local:
         concurrency: 0