diff --git a/ldap.Dockerfile b/ldap.Dockerfile
index 676daff58..bfcc3dae6 100644
--- a/ldap.Dockerfile
+++ b/ldap.Dockerfile
@@ -19,7 +19,7 @@ ENV GIT_BUILD_HASH=$GIT_BUILD_HASH
 
 COPY --from=builder /go/ldap /
 
-HEALTHCHECK CMD [ "wget", "--spider", "http://localhost:9300/outpost.goauthentik.io/ping" ]
+HEALTHCHECK --interval=5s --retries=10 --start-period=3s CMD [ "wget", "--spider", "http://localhost:9300/outpost.goauthentik.io/ping" ]
 
 EXPOSE 3389 6636 9300
 
diff --git a/proxy.Dockerfile b/proxy.Dockerfile
index 52de9ef93..6a5da8b3d 100644
--- a/proxy.Dockerfile
+++ b/proxy.Dockerfile
@@ -32,7 +32,7 @@ COPY --from=web-builder /static/security.txt /web/security.txt
 COPY --from=web-builder /static/dist/ /web/dist/
 COPY --from=web-builder /static/authentik/ /web/authentik/
 
-HEALTHCHECK CMD [ "wget", "--spider", "http://localhost:9300/outpost.goauthentik.io/ping" ]
+HEALTHCHECK --interval=5s --retries=10 --start-period=3s CMD [ "wget", "--spider", "http://localhost:9300/outpost.goauthentik.io/ping" ]
 
 EXPOSE 9000 9300 9443