diff --git a/.github/workflows/goreleaser-fleet.yaml b/.github/workflows/goreleaser-fleet.yaml
index 0db71f3b0e..d1e61904af 100644
--- a/.github/workflows/goreleaser-fleet.yaml
+++ b/.github/workflows/goreleaser-fleet.yaml
@@ -124,6 +124,19 @@ jobs:
           subject-name: "docker.io/fleetdm/fleetctl"
           push-to-registry: true
 
+      - name: Update fleetdm/fleet:latest and fleetdm/fleetctl:latest
+        run: |
+          highest_release=$(gh api -H "Accept: application/vnd.github+json" -H "X-GitHub-Api-Version: 2022-11-28" /repos/fleetdm/fleet/releases | jq -r '.[].tag_name' | sort -r | head -n 1 | sed -e "s/^fleet-//")
+          tag=${{ steps.docker.outputs.tag }}
+          if [[ $(printf "$highest_release\n$tag" | sort -r | head -n 1) = "$tag" ]]; then
+            docker tag fleetdm/fleet:$tag fleetdm/fleet:latest
+            docker push fleetdm/fleet:latest
+            docker tag fleetdm/fleetctl:$tag fleetdm/fleetctl:latest
+            docker push fleetdm/fleetctl:latest
+          else
+            echo "Skipping tagging of fleetdm/fleet:latest and fleetdm/fleetctl:latest because existing release $highest_release is higher than $tag"
+          fi
+
       - name: List tags for push
         run: |
           echo "The following TAGs are to be pushed: ${{ steps.docker.outputs.TAG }}"
@@ -138,6 +151,6 @@ jobs:
       - name: Tag and push to quay.io
         run: |
           for TAG in ${{ steps.docker.outputs.TAG }}; do
-          docker tag fleetdm/fleet:${TAG} quay.io/fleetdm/fleet:${TAG}
-          docker push quay.io/fleetdm/fleet:${TAG}
+            docker tag fleetdm/fleet:${TAG} quay.io/fleetdm/fleet:${TAG}
+            docker push quay.io/fleetdm/fleet:${TAG}
           done
diff --git a/.goreleaser.yml b/.goreleaser.yml
index b2d3823768..ed8438d9e2 100644
--- a/.goreleaser.yml
+++ b/.goreleaser.yml
@@ -119,10 +119,8 @@ dockers:
       - fleetctl
     dockerfile: tools/fleet-docker/Dockerfile
     image_templates:
-      - 'fleetdm/fleet:latest'
-      - 'fleetdm/fleet:{{ .Tag }}'
-      - 'fleetdm/fleet:{{ .Tag }}'
-      - 'fleetdm/fleet:v{{ .Major }}'
+      - "fleetdm/fleet:{{ .Tag }}"
+      - "fleetdm/fleet:v{{ .Major }}"
 
   - goos: linux
     goarch: amd64
@@ -132,13 +130,11 @@ dockers:
     build_flag_templates:
       - "--build-arg=binpath=fleetctl"
     image_templates:
-      - 'fleetdm/fleetctl:latest'
-      - 'fleetdm/fleetctl:{{ .Tag }}'
-      - 'fleetdm/fleetctl:{{ .Tag }}'
-      - 'fleetdm/fleetctl:v{{ .Major }}'
+      - "fleetdm/fleetctl:{{ .Tag }}"
+      - "fleetdm/fleetctl:v{{ .Major }}"
 
 checksum:
-  name_template: 'checksums.txt'
+  name_template: "checksums.txt"
 
 snapshot:
   version_template: "{{ .Tag }}-untagged"