diff --git a/lib/mrsk/commands/prune.rb b/lib/mrsk/commands/prune.rb
index 79da58be..3b68fe3f 100644
--- a/lib/mrsk/commands/prune.rb
+++ b/lib/mrsk/commands/prune.rb
@@ -3,12 +3,15 @@ require "active_support/core_ext/numeric/time"
 
 class Mrsk::Commands::Prune < Mrsk::Commands::Base
   def images
-    docker :image, :prune, "--force", "--filter", "label=service=#{config.service}", "--filter", "dangling=true"
+    pipe \
+      docker(:image, :ls, *service_filter, "--format", "'{{.Repository}}:{{.Tag}}'"),
+      "grep -v -w \"#{active_image_list}\"",
+      "while read tag; do docker rmi $tag; done"
   end
 
   def containers(keep_last: 5)
     pipe \
-      docker(:ps, "-q", "-a", "--filter", "label=service=#{config.service}", *stopped_containers_filters),
+      docker(:ps, "-q", "-a", *service_filter, *stopped_containers_filters),
       "tail -n +#{keep_last + 1}",
       "while read container_id; do docker rm $container_id; done"
   end
@@ -17,4 +20,12 @@ class Mrsk::Commands::Prune < Mrsk::Commands::Base
     def stopped_containers_filters
       [ "created", "exited", "dead" ].flat_map { |status| ["--filter", "status=#{status}"] }
     end
+
+    def active_image_list
+      "$(docker container ls -a --format '{{.Image}}\\|' --filter label=service=#{config.service} | tr -d '\\n')#{config.latest_image}"
+    end
+
+    def service_filter
+      [ "--filter", "label=service=#{config.service}" ]
+    end
 end
diff --git a/test/cli/prune_test.rb b/test/cli/prune_test.rb
index e07f3172..85cdf159 100644
--- a/test/cli/prune_test.rb
+++ b/test/cli/prune_test.rb
@@ -10,7 +10,7 @@ class CliPruneTest < CliTestCase
 
   test "images" do
     run_command("images").tap do |output|
-      assert_match /docker image prune --force --filter label=service=app --filter dangling=true on 1.1.1.\d/, output
+      assert_match "docker image ls --filter label=service=app --format '{{.Repository}}:{{.Tag}}' | grep -v -w \"$(docker container ls -a --format '{{.Image}}\\|' --filter label=service=app | tr -d '\\n')dhh/app:latest\" | while read tag; do docker rmi $tag; done on 1.1.1.", output
     end
   end
 
diff --git a/test/commands/prune_test.rb b/test/commands/prune_test.rb
index 436ed02f..f4025893 100644
--- a/test/commands/prune_test.rb
+++ b/test/commands/prune_test.rb
@@ -10,7 +10,7 @@ class CommandsPruneTest < ActiveSupport::TestCase
 
   test "images" do
     assert_equal \
-      "docker image prune --force --filter label=service=app --filter dangling=true",
+      "docker image ls --filter label=service=app --format '{{.Repository}}:{{.Tag}}' | grep -v -w \"$(docker container ls -a --format '{{.Image}}\\|' --filter label=service=app | tr -d '\\n')dhh/app:latest\" | while read tag; do docker rmi $tag; done",
       new_command.images.join(" ")
   end