diff --git a/Tiltfile b/Tiltfile
index a69726af..36c781af 100644
--- a/Tiltfile
+++ b/Tiltfile
@@ -19,8 +19,8 @@ settings = {
     "deploy_cert_manager": True,
     "preload_images_for_kind": True,
     "kind_cluster_name": "capoci",
-    "capi_version": "v1.3.0",
-    "cert_manager_version": "v1.1.0",
+    "capi_version": "v1.4.1",
+    "cert_manager_version": "v1.11.0",
     "kubernetes_version": "v1.24.3",
 }
 
@@ -41,18 +41,22 @@ if "default_registry" in settings:
 
 tilt_helper_dockerfile_header = """
 # Tilt image
-FROM golang:1.18 as tilt-helper
+FROM golang:1.19 as tilt-helper
 # Support live reloading with Tilt
-RUN wget --output-document /restart.sh --quiet https://raw.githubusercontent.com/windmilleng/rerun-process-wrapper/master/restart.sh  && \
-    wget --output-document /start.sh --quiet https://raw.githubusercontent.com/windmilleng/rerun-process-wrapper/master/start.sh && \
-    chmod +x /start.sh && chmod +x /restart.sh
+RUN go install github.com/go-delve/delve/cmd/dlv@latest
+RUN wget --output-document /restart.sh --quiet https://raw.githubusercontent.com/tilt-dev/rerun-process-wrapper/master/restart.sh  && \
+    wget --output-document /start.sh --quiet https://raw.githubusercontent.com/tilt-dev/rerun-process-wrapper/master/start.sh && \
+    chmod +x /start.sh && chmod +x /restart.sh && chmod +x /go/bin/dlv && \
+    touch /process.txt && chmod 0777 /process.txt `# pre-create PID file to allow even non-root users to run the image`
 """
 
 tilt_dockerfile_header = """
 FROM gcr.io/distroless/base:debug as tilt
 WORKDIR /
+COPY --from=tilt-helper /process.txt .
 COPY --from=tilt-helper /start.sh .
 COPY --from=tilt-helper /restart.sh .
+COPY --from=tilt-helper /go/bin/dlv .
 COPY manager .
 """