diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 8487e4d3c3..b535428086 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -19,7 +19,7 @@ on:
 
 jobs:
   prepare:
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-22.04
     outputs:
       matrix: ${{ steps.platforms.outputs.matrix }}
     steps:
@@ -37,7 +37,7 @@ jobs:
           echo ${{ steps.platforms.outputs.matrix }}
 
   build:
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-22.04
     needs:
       - prepare
     strategy:
@@ -90,7 +90,7 @@ jobs:
           if-no-files-found: error
 
   bin-image:
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-22.04
     if: ${{ github.event_name != 'pull_request' && github.repository == 'docker/cli' }}
     steps:
       -
@@ -134,7 +134,7 @@ jobs:
             *.cache-to=type=gha,scope=bin-image,mode=max
 
   prepare-plugins:
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-22.04
     outputs:
       matrix: ${{ steps.platforms.outputs.matrix }}
     steps:
@@ -152,7 +152,7 @@ jobs:
           echo ${{ steps.platforms.outputs.matrix }}
 
   plugins:
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-22.04
     needs:
       - prepare-plugins
     strategy:
diff --git a/.github/workflows/e2e.yml b/.github/workflows/e2e.yml
index 67ffdff09d..227d105f8e 100644
--- a/.github/workflows/e2e.yml
+++ b/.github/workflows/e2e.yml
@@ -16,7 +16,7 @@ on:
 
 jobs:
   e2e:
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-22.04
     strategy:
       fail-fast: false
       matrix:
@@ -28,11 +28,11 @@ jobs:
           - alpine
           - debian
         engine-version:
-#          - 20.10-dind # FIXME: Fails on 20.10
-          - stable-dind # TODO: Use 20.10-dind, stable-dind is deprecated
-        include:
-          - target: non-experimental
-            engine-version: 19.03-dind
+          - 25.0  # latest
+          - 24.0  # latest - 1
+          - 23.0  # mirantis lts
+          # TODO(krissetto) 19.03 needs a look, doesn't work ubuntu 22.04 (cgroup errors). 
+          # we could have a separate job that tests it against ubuntu 20.04
     steps:
       -
         name: Checkout
diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 5cf04b3372..1a8ce1f291 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -16,7 +16,7 @@ on:
 
 jobs:
   ctn:
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-22.04
     steps:
       -
         name: Checkout
diff --git a/.github/workflows/validate.yml b/.github/workflows/validate.yml
index ccd0493a32..41349713c8 100644
--- a/.github/workflows/validate.yml
+++ b/.github/workflows/validate.yml
@@ -16,7 +16,7 @@ on:
 
 jobs:
   validate:
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-22.04
     strategy:
       fail-fast: false
       matrix:
@@ -37,7 +37,7 @@ jobs:
 
   # check that the generated Markdown and the checked-in files match
   validate-md:
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-22.04
     steps:
       -
         name: Checkout
@@ -57,7 +57,7 @@ jobs:
           fi
 
   validate-make:
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-22.04
     strategy:
       fail-fast: false
       matrix:
diff --git a/e2e/image/testdata/pull-with-content-trust.golden b/e2e/image/testdata/pull-with-content-trust.golden
index b21407e117..582a4e0cc9 100644
--- a/e2e/image/testdata/pull-with-content-trust.golden
+++ b/e2e/image/testdata/pull-with-content-trust.golden
@@ -1,5 +1,5 @@
 Pull (1 of 1): registry:5000/trust-pull:latest@sha256:e2e16842c9b54d985bf1ef9242a313f36b856181f188de21313820e177002501
-sha256:e2e16842c9b54d985bf1ef9242a313f36b856181f188de21313820e177002501: Pulling from trust-pull
+registry:5000/trust-pull@sha256:e2e16842c9b54d985bf1ef9242a313f36b856181f188de21313820e177002501: Pulling from trust-pull
 Digest: sha256:e2e16842c9b54d985bf1ef9242a313f36b856181f188de21313820e177002501
 Status: Downloaded newer image for registry:5000/trust-pull@sha256:e2e16842c9b54d985bf1ef9242a313f36b856181f188de21313820e177002501
 registry:5000/trust-pull:latest
diff --git a/e2e/plugin/trust_test.go b/e2e/plugin/trust_test.go
index 38bdcc5e45..c6957d6f37 100644
--- a/e2e/plugin/trust_test.go
+++ b/e2e/plugin/trust_test.go
@@ -11,6 +11,7 @@ import (
 	"github.com/docker/cli/e2e/internal/fixtures"
 	"github.com/docker/cli/internal/test/environment"
 	"github.com/docker/docker/api/types"
+	"github.com/docker/docker/api/types/versions"
 	"github.com/pkg/errors"
 	"gotest.tools/v3/assert"
 	"gotest.tools/v3/fs"
@@ -21,6 +22,8 @@ import (
 const registryPrefix = "registry:5000"
 
 func TestInstallWithContentTrust(t *testing.T) {
+	// TODO(krissetto): remove this skip once the fix (see https://github.com/moby/moby/pull/47299) is deployed to moby versions < 25
+	skip.If(t, versions.LessThan(environment.DaemonAPIVersion(t), "1.44"))
 	skip.If(t, environment.SkipPluginTests())
 
 	pluginName := fmt.Sprintf("%s/plugin-content-trust", registryPrefix)
@@ -50,7 +53,7 @@ func TestInstallWithContentTrust(t *testing.T) {
 		fixtures.WithNotary,
 	)
 	result.Assert(t, icmd.Expected{
-		Out: fmt.Sprintf("Status: Downloaded newer image for %s@sha", pluginName),
+		Out: fmt.Sprintf("Installed plugin %s", pluginName),
 	})
 }