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..9ce1a6d92a 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
@@ -55,7 +55,7 @@ jobs:
           make -f docker.Makefile test-e2e-${{ matrix.target }}
         env:
           BASE_VARIANT: ${{ matrix.base }}
-          E2E_ENGINE_VERSION: ${{ matrix.engine-version }}
+          ENGINE_VERSION: ${{ matrix.engine-version }}
           TESTFLAGS: -coverprofile=/tmp/coverage/coverage.txt
       -
         name: Send to Codecov
diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 447c570914..db37d7db7a 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/docker.Makefile b/docker.Makefile
index bddd91a2a5..011bfd9b68 100644
--- a/docker.Makefile
+++ b/docker.Makefile
@@ -14,13 +14,13 @@ PACKAGER_NAME ?=
 
 DEV_DOCKER_IMAGE_NAME = docker-cli-dev$(IMAGE_TAG)
 E2E_IMAGE_NAME = docker-cli-e2e
-E2E_ENGINE_VERSION ?=
+ENGINE_VERSION ?=
 CACHE_VOLUME_NAME := docker-cli-dev-cache
 ifeq ($(DOCKER_CLI_GO_BUILD_CACHE),y)
 DOCKER_CLI_MOUNTS += -v "$(CACHE_VOLUME_NAME):/root/.cache/go-build"
 endif
 VERSION = $(shell cat VERSION)
-ENVVARS = -e VERSION=$(VERSION) -e GITCOMMIT -e PLATFORM -e TESTFLAGS -e TESTDIRS -e GOOS -e GOARCH -e GOARM -e TEST_ENGINE_VERSION=$(E2E_ENGINE_VERSION)
+ENVVARS = -e VERSION=$(VERSION) -e GITCOMMIT -e PLATFORM -e TESTFLAGS -e TESTDIRS -e GOOS -e GOARCH -e GOARM -e ENGINE_VERSION
 
 # Some Dockerfiles use features that are only supported with BuildKit enabled
 export DOCKER_BUILDKIT=1
@@ -132,21 +132,21 @@ test-e2e: test-e2e-non-experimental test-e2e-experimental test-e2e-connhelper-ss
 
 .PHONY: test-e2e-experimental
 test-e2e-experimental: build-e2e-image # run experimental e2e tests
-	docker run --rm $(ENVVARS) -e DOCKERD_EXPERIMENTAL=1 -e TEST_ENGINE_VERSION=$(E2E_ENGINE_VERSION) \
+	docker run --rm $(ENVVARS) -e DOCKERD_EXPERIMENTAL=1 \
 		--mount type=bind,src=$(CURDIR)/build/coverage,dst=/tmp/coverage \
 		--mount type=bind,src=/var/run/docker.sock,dst=/var/run/docker.sock \
 		$(E2E_IMAGE_NAME)
 
 .PHONY: test-e2e-non-experimental
 test-e2e-non-experimental: build-e2e-image # run non-experimental e2e tests
-	docker run --rm $(ENVVARS) -e TEST_ENGINE_VERSION=$(E2E_ENGINE_VERSION) \
+	docker run --rm $(ENVVARS) \
 		--mount type=bind,src=$(CURDIR)/build/coverage,dst=/tmp/coverage \
 		--mount type=bind,src=/var/run/docker.sock,dst=/var/run/docker.sock \
 		$(E2E_IMAGE_NAME)
 
 .PHONY: test-e2e-connhelper-ssh
 test-e2e-connhelper-ssh: build-e2e-image # run experimental SSH-connection helper e2e tests
-	docker run --rm $(ENVVARS) -e DOCKERD_EXPERIMENTAL=1 -e TEST_ENGINE_VERSION=$(E2E_ENGINE_VERSION) -e TEST_CONNHELPER=ssh \
+	docker run --rm $(ENVVARS) -e DOCKERD_EXPERIMENTAL=1 -e TEST_CONNHELPER=ssh \
 		--mount type=bind,src=$(CURDIR)/build/coverage,dst=/tmp/coverage \
 		--mount type=bind,src=/var/run/docker.sock,dst=/var/run/docker.sock \
 		$(E2E_IMAGE_NAME)
diff --git a/e2e/compose-env.connhelper-ssh.yaml b/e2e/compose-env.connhelper-ssh.yaml
index 2a91ab48fe..283e306fbc 100644
--- a/e2e/compose-env.connhelper-ssh.yaml
+++ b/e2e/compose-env.connhelper-ssh.yaml
@@ -3,5 +3,7 @@ services:
       build:
         context: ./testdata
         dockerfile: Dockerfile.connhelper-ssh
+        args: 
+          - ENGINE_VERSION
       environment:
         - TEST_CONNHELPER_SSH_ID_RSA_PUB
diff --git a/e2e/compose-env.yaml b/e2e/compose-env.yaml
index 9eade791b0..2a30e1040e 100644
--- a/e2e/compose-env.yaml
+++ b/e2e/compose-env.yaml
@@ -1,9 +1,10 @@
 services:
+
   registry:
     image: 'registry:2'
 
   engine:
-      image: 'docker:${TEST_ENGINE_VERSION:-stable-dind}'
+      image: 'docker:${ENGINE_VERSION:-25.0}-dind'
       privileged: true
       command: ['--insecure-registry=registry:5000']
       environment:
@@ -16,6 +17,7 @@ services:
       ports:
         - 4443:4443
       command: ['notary-server', '-config=/fixtures/notary-config.json']
+
   evil-notary-server:
       build:
         context: ./testdata
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),
 	})
 }
 
diff --git a/e2e/testdata/Dockerfile.connhelper-ssh b/e2e/testdata/Dockerfile.connhelper-ssh
index 64306b518c..3771f3e62f 100644
--- a/e2e/testdata/Dockerfile.connhelper-ssh
+++ b/e2e/testdata/Dockerfile.connhelper-ssh
@@ -1,5 +1,16 @@
-FROM docker:test-dind
-RUN apk --no-cache add shadow openssh-server && \
+# syntax=docker/dockerfile:1
+
+# ENGINE_VERSION is the version of the (docker-in-docker) Docker Engine to
+# test against.
+ARG ENGINE_VERSION=25.0
+
+FROM docker:${ENGINE_VERSION}-dind
+
+# the openssh-client update is needed for security reasons when using docker:23.0-dind, currently maintained as an lts by mirantis
+RUN apk --no-cache upgrade openssh-client && \
+  apk --no-cache add shadow openssh-server && \
+  # TODO(krissetto): `groupadd` can be removed once we only test against moby >= v24
+  # see https://github.com/docker-library/docker/pull/470
   groupadd -f docker && \
   useradd --create-home --shell /bin/sh --password $(head -c32 /dev/urandom | base64) penguin && \
   usermod -aG docker penguin && \
diff --git a/e2e/testdata/Dockerfile.evil-notary-server b/e2e/testdata/Dockerfile.evil-notary-server
index d982d5a4eb..97f234e849 100644
--- a/e2e/testdata/Dockerfile.evil-notary-server
+++ b/e2e/testdata/Dockerfile.evil-notary-server
@@ -1,4 +1,7 @@
+# syntax=docker/dockerfile:1
+
 ARG NOTARY_VERSION=0.6.1
+
 FROM notary:server-${NOTARY_VERSION}
 
 COPY ./notary-evil/ /fixtures/
diff --git a/e2e/testdata/Dockerfile.notary-server b/e2e/testdata/Dockerfile.notary-server
index 4bc59d2d88..846253e2fb 100644
--- a/e2e/testdata/Dockerfile.notary-server
+++ b/e2e/testdata/Dockerfile.notary-server
@@ -1,4 +1,7 @@
+# syntax=docker/dockerfile:1
+
 ARG NOTARY_VERSION=0.6.1
+
 FROM notary:server-${NOTARY_VERSION}
 
 COPY ./notary/ /fixtures/
diff --git a/internal/test/environment/testenv.go b/internal/test/environment/testenv.go
index 8b035fca1b..7fe6880244 100644
--- a/internal/test/environment/testenv.go
+++ b/internal/test/environment/testenv.go
@@ -108,3 +108,14 @@ func SkipIfNotPlatform(t *testing.T, platform string) {
 	daemonPlatform := strings.TrimSpace(result.Stdout())
 	skip.If(t, daemonPlatform != platform, "running against a non %s daemon", platform)
 }
+
+// DaemonAPIVersion returns the negotiated daemon API version.
+func DaemonAPIVersion(t *testing.T) string {
+	t.Helper()
+	// Use Client.APIVersion instead of Server.APIVersion.
+	// The latter is the maximum version that the server supports
+	// while the Client.APIVersion contains the negotiated version.
+	result := icmd.RunCmd(icmd.Command("docker", "version", "--format", "{{.Client.APIVersion}}"))
+	result.Assert(t, icmd.Expected{Err: icmd.None})
+	return strings.TrimSpace(result.Stdout())
+}