diff --git a/.github/workflows/pr-ci.yml b/.github/workflows/pr-ci.yml
index 37cda2893..58726af3e 100644
--- a/.github/workflows/pr-ci.yml
+++ b/.github/workflows/pr-ci.yml
@@ -399,6 +399,16 @@ jobs:
             job-timeout-minutes: 20
             flake-attempts: 2
 
+          - label: up-provider-podman-rootless-exec
+            runner: ubuntu-latest
+            free-disk-space: false
+            install-kind: false
+            requires-secret: false
+            install-podman: rootless
+            test-timeout: 600s
+            job-timeout-minutes: 20
+            flake-attempts: 2
+
           - label: up-provider-podman-rootless-lifecycle
             runner: ubuntu-latest
             free-disk-space: true
@@ -449,6 +459,16 @@ jobs:
             job-timeout-minutes: 20
             flake-attempts: 2
 
+          - label: up-provider-podman-rootful-lifecycle-2
+            runner: ubuntu-latest
+            free-disk-space: true
+            install-kind: false
+            requires-secret: false
+            install-podman: rootful
+            test-timeout: 600s
+            job-timeout-minutes: 20
+            flake-attempts: 2
+
           - label: up-provider-podman-rootful-config
             runner: ubuntu-latest
             free-disk-space: true
diff --git a/e2e/tests/up/provider_podman_rootful_lifecycle.go b/e2e/tests/up/provider_podman_rootful_lifecycle.go
index f050289b2..0412b75e8 100644
--- a/e2e/tests/up/provider_podman_rootful_lifecycle.go
+++ b/e2e/tests/up/provider_podman_rootful_lifecycle.go
@@ -4,7 +4,6 @@ import (
 	"context"
 	"os"
 	"os/exec"
-	"path/filepath"
 	"strings"
 	"time"
 
@@ -220,119 +219,6 @@ var _ = ginkgo.Describe(
 					},
 					ginkgo.SpecTimeout(framework.TimeoutShort()),
 				)
-
-				ginkgo.It(
-					"should run postAttachCommand on every attach",
-					func(ctx context.Context) {
-						tempDir, err := setupWorkspace(
-							"tests/up/testdata/docker-post-attach-every-time",
-							initialDir,
-							f,
-						)
-						framework.ExpectNoError(err)
-
-						err = f.DevsyUp(ctx, tempDir)
-						framework.ExpectNoError(err)
-
-						gomega.Eventually(func() string {
-							out, err := f.DevsySSH(
-								ctx, tempDir, "cat $HOME/attach-count.out 2>/dev/null",
-							)
-							if err != nil {
-								return ""
-							}
-							return strings.TrimSpace(out)
-						}).WithTimeout(15 * time.Second).WithPolling(1 * time.Second).Should(
-							gomega.Equal("1"),
-						)
-
-						err = f.DevsyUp(ctx, tempDir)
-						framework.ExpectNoError(err)
-
-						gomega.Eventually(func() string {
-							out, err := f.DevsySSH(
-								ctx, tempDir, "cat $HOME/attach-count.out 2>/dev/null",
-							)
-							if err != nil {
-								return ""
-							}
-							return strings.TrimSpace(out)
-						}).WithTimeout(15 * time.Second).WithPolling(1 * time.Second).Should(
-							gomega.Equal("2"),
-						)
-					},
-					ginkgo.SpecTimeout(
-						framework.TimeoutModerate(),
-					),
-				)
-
-				ginkgo.It(
-					"should run initializeCommand with object syntax",
-					func(ctx context.Context) {
-						tempDir, err := setupWorkspaceAndUp(
-							ctx,
-							"tests/up/testdata/docker-initcmd-parallel",
-							initialDir,
-							f,
-						)
-						framework.ExpectNoError(err)
-
-						one, err := os.ReadFile( //nolint:gosec // G304
-							filepath.Join(tempDir, "init-cmd-one.out"),
-						)
-						framework.ExpectNoError(err)
-						gomega.Expect(string(one)).To(gomega.Equal("initCmdOne"))
-
-						two, err := os.ReadFile( //nolint:gosec // G304
-							filepath.Join(tempDir, "init-cmd-two.out"),
-						)
-						framework.ExpectNoError(err)
-						gomega.Expect(string(two)).To(gomega.Equal("initCmdTwo"))
-					},
-					ginkgo.SpecTimeout(framework.TimeoutShort()),
-				)
-
-				ginkgo.It(
-					"should inject secrets-file env into lifecycle commands",
-					func(ctx context.Context) {
-						tempDir, err := setupWorkspace(
-							"tests/up/testdata/docker-secrets-file",
-							initialDir,
-							f,
-						)
-						framework.ExpectNoError(err)
-
-						secretsDir, err := framework.CreateTempDir()
-						framework.ExpectNoError(err)
-						ginkgo.DeferCleanup(func() { _ = os.RemoveAll(secretsDir) })
-
-						secretsFile := filepath.Join(secretsDir, "secrets.json")
-						err = os.WriteFile(
-							secretsFile,
-							[]byte(
-								`{"MY_SECRET":"test-value-12345","ANOTHER_SECRET":"second-secret-42"}`,
-							),
-							0o600,
-						)
-						framework.ExpectNoError(err)
-
-						err = f.DevsyUp(ctx, tempDir, "--secrets-file", secretsFile)
-						framework.ExpectNoError(err)
-
-						out, err := f.DevsySSH(ctx, tempDir, "cat /tmp/secret-check.out")
-						framework.ExpectNoError(err)
-						gomega.Expect(strings.TrimSpace(out)).
-							To(gomega.Equal("test-value-12345"))
-
-						out, err = f.DevsySSH(
-							ctx, tempDir, "cat /tmp/another-secret-check.out",
-						)
-						framework.ExpectNoError(err)
-						gomega.Expect(strings.TrimSpace(out)).
-							To(gomega.Equal("second-secret-42"))
-					},
-					ginkgo.SpecTimeout(framework.TimeoutShort()),
-				)
 			})
 		})
 	},
diff --git a/e2e/tests/up/provider_podman_rootful_lifecycle_2.go b/e2e/tests/up/provider_podman_rootful_lifecycle_2.go
new file mode 100644
index 000000000..21f6db91c
--- /dev/null
+++ b/e2e/tests/up/provider_podman_rootful_lifecycle_2.go
@@ -0,0 +1,187 @@
+package up
+
+import (
+	"context"
+	"os"
+	"os/exec"
+	"path/filepath"
+	"strings"
+	"time"
+
+	"github.com/devsy-org/devsy/e2e/framework"
+	"github.com/devsy-org/devsy/pkg/docker"
+	"github.com/onsi/ginkgo/v2"
+	"github.com/onsi/gomega"
+)
+
+var _ = ginkgo.Describe(
+	"testing up command for podman provider",
+	ginkgo.Label("up-provider-podman-rootful-lifecycle-2"),
+	func() {
+		var initialDir string
+
+		ginkgo.BeforeEach(func() {
+			var err error
+			initialDir, err = os.Getwd()
+			framework.ExpectNoError(err)
+		})
+
+		ginkgo.Context("with rootful podman", func() {
+			var f *framework.Framework
+
+			//nolint:dupl // shared rootful podman wrapper setup across split files
+			ginkgo.BeforeEach(func(ctx context.Context) {
+				wrapper, err := os.Create( //nolint:gosec // G304: test-controlled path
+					initialDir + "/bin/podman-rootful",
+				)
+				framework.ExpectNoError(err)
+
+				_, err = wrapper.WriteString("#!/bin/sh\nsudo podman \"$@\"\n")
+				if err != nil {
+					_ = wrapper.Close()
+					framework.ExpectNoError(err)
+				}
+
+				err = wrapper.Close()
+				framework.ExpectNoError(err)
+
+				// #nosec G302 -- wrapper script needs execute permission
+				err = os.Chmod(initialDir+"/bin/podman-rootful", 0o755)
+				framework.ExpectNoError(err)
+
+				cmd := exec.CommandContext( //nolint:gosec // G204: test-controlled path
+					ctx, initialDir+"/bin/podman-rootful", "ps",
+				)
+				docker.PrepareForGroupCancellation(cmd)
+				out, err := cmd.CombinedOutput()
+				framework.ExpectNoError(err, string(out))
+
+				ginkgo.DeferCleanup(func() {
+					_ = os.Remove(initialDir + "/bin/podman-rootful")
+				})
+
+				f, err = setupDockerProvider(
+					initialDir+"/bin",
+					initialDir+"/bin/podman-rootful",
+				)
+				framework.ExpectNoError(err)
+			},
+			)
+
+			ginkgo.Context("lifecycle commands", func() { //nolint:dupl
+				ginkgo.It(
+					"should run postAttachCommand on every attach",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace(
+							"tests/up/testdata/docker-post-attach-every-time",
+							initialDir,
+							f,
+						)
+						framework.ExpectNoError(err)
+
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+
+						gomega.Eventually(func() string {
+							out, err := f.DevsySSH(
+								ctx, tempDir, "cat $HOME/attach-count.out 2>/dev/null",
+							)
+							if err != nil {
+								return ""
+							}
+							return strings.TrimSpace(out)
+						}).WithTimeout(15 * time.Second).WithPolling(1 * time.Second).Should(
+							gomega.Equal("1"),
+						)
+
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+
+						gomega.Eventually(func() string {
+							out, err := f.DevsySSH(
+								ctx, tempDir, "cat $HOME/attach-count.out 2>/dev/null",
+							)
+							if err != nil {
+								return ""
+							}
+							return strings.TrimSpace(out)
+						}).WithTimeout(15 * time.Second).WithPolling(1 * time.Second).Should(
+							gomega.Equal("2"),
+						)
+					},
+					ginkgo.SpecTimeout(
+						framework.TimeoutModerate(),
+					),
+				)
+
+				ginkgo.It(
+					"should run initializeCommand with object syntax",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspaceAndUp(
+							ctx,
+							"tests/up/testdata/docker-initcmd-parallel",
+							initialDir,
+							f,
+						)
+						framework.ExpectNoError(err)
+
+						one, err := os.ReadFile( //nolint:gosec // G304
+							filepath.Join(tempDir, "init-cmd-one.out"),
+						)
+						framework.ExpectNoError(err)
+						gomega.Expect(string(one)).To(gomega.Equal("initCmdOne"))
+
+						two, err := os.ReadFile( //nolint:gosec // G304
+							filepath.Join(tempDir, "init-cmd-two.out"),
+						)
+						framework.ExpectNoError(err)
+						gomega.Expect(string(two)).To(gomega.Equal("initCmdTwo"))
+					},
+					ginkgo.SpecTimeout(framework.TimeoutShort()),
+				)
+
+				ginkgo.It( //nolint:dupl // mirrors rootless lifecycle secrets-file test
+					"should inject secrets-file env into lifecycle commands",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace(
+							"tests/up/testdata/docker-secrets-file",
+							initialDir,
+							f,
+						)
+						framework.ExpectNoError(err)
+
+						secretsDir, err := framework.CreateTempDir()
+						framework.ExpectNoError(err)
+						ginkgo.DeferCleanup(func() { _ = os.RemoveAll(secretsDir) })
+
+						secretsFile := filepath.Join(secretsDir, "secrets.json")
+						err = os.WriteFile(
+							secretsFile,
+							[]byte(
+								`{"MY_SECRET":"test-value-12345","ANOTHER_SECRET":"second-secret-42"}`,
+							),
+							0o600,
+						)
+						framework.ExpectNoError(err)
+
+						err = f.DevsyUp(ctx, tempDir, "--secrets-file", secretsFile)
+						framework.ExpectNoError(err)
+
+						out, err := f.DevsySSH(ctx, tempDir, "cat /tmp/secret-check.out")
+						framework.ExpectNoError(err)
+						gomega.Expect(strings.TrimSpace(out)).
+							To(gomega.Equal("test-value-12345"))
+
+						out, err = f.DevsySSH(
+							ctx, tempDir, "cat /tmp/another-secret-check.out",
+						)
+						framework.ExpectNoError(err)
+						gomega.Expect(strings.TrimSpace(out)).
+							To(gomega.Equal("second-secret-42"))
+					},
+					ginkgo.SpecTimeout(framework.TimeoutShort()),
+				)
+			})
+		})
+	},
+)
diff --git a/e2e/tests/up/provider_podman_rootless_basic.go b/e2e/tests/up/provider_podman_rootless_basic.go
index 9ed047aca..88e5ceefb 100644
--- a/e2e/tests/up/provider_podman_rootless_basic.go
+++ b/e2e/tests/up/provider_podman_rootless_basic.go
@@ -107,69 +107,6 @@ var _ = ginkgo.Describe(
 					ginkgo.SpecTimeout(framework.TimeoutShort()),
 				)
 			})
-
-			ginkgo.Context("agent delivery", func() {
-				ginkgo.It(
-					"should deliver the agent binary and execute SSH commands",
-					func(ctx context.Context) {
-						tempDir, err := setupWorkspace("tests/up/testdata/docker", initialDir, f)
-						framework.ExpectNoError(err)
-
-						err = f.DevsyUp(ctx, tempDir)
-						framework.ExpectNoError(err)
-
-						err = f.DevsySSHEchoTestString(ctx, tempDir)
-						framework.ExpectNoError(err)
-					},
-					ginkgo.SpecTimeout(framework.TimeoutShort()),
-				)
-			})
-
-			ginkgo.Context("exec", func() {
-				ginkgo.It(
-					"should execute commands inside the container via SSH",
-					func(ctx context.Context) {
-						tempDir, err := setupWorkspace("tests/up/testdata/docker", initialDir, f)
-						framework.ExpectNoError(err)
-
-						err = f.DevsyUp(ctx, tempDir)
-						framework.ExpectNoError(err)
-
-						out, err := f.DevsySSH(ctx, tempDir, "echo -n hello-podman")
-						framework.ExpectNoError(err)
-						framework.ExpectEqual(out, "hello-podman")
-
-						out, err = f.DevsySSH(ctx, tempDir, "pwd")
-						framework.ExpectNoError(err)
-						gomega.Expect(strings.TrimSpace(out)).NotTo(gomega.BeEmpty())
-					},
-					ginkgo.SpecTimeout(framework.TimeoutShort()),
-				)
-			})
-
-			ginkgo.Context("cleanup", func() {
-				ginkgo.It(
-					"should delete workspace and clean up resources",
-					func(ctx context.Context) {
-						tempDir, err := framework.CopyToTempDir("tests/up/testdata/docker")
-						framework.ExpectNoError(err)
-						ginkgo.DeferCleanup(framework.CleanupTempDir, initialDir, tempDir)
-
-						err = f.DevsyUp(ctx, tempDir)
-						framework.ExpectNoError(err)
-
-						_, err = f.FindWorkspace(ctx, tempDir)
-						framework.ExpectNoError(err)
-
-						err = f.DevsyWorkspaceDelete(ctx, tempDir)
-						framework.ExpectNoError(err)
-
-						_, err = f.FindWorkspace(ctx, tempDir)
-						framework.ExpectError(err)
-					},
-					ginkgo.SpecTimeout(framework.TimeoutShort()),
-				)
-			})
 		})
 	},
 )
diff --git a/e2e/tests/up/provider_podman_rootless_exec.go b/e2e/tests/up/provider_podman_rootless_exec.go
new file mode 100644
index 000000000..ab6c1f5a7
--- /dev/null
+++ b/e2e/tests/up/provider_podman_rootless_exec.go
@@ -0,0 +1,98 @@
+package up
+
+import (
+	"context"
+	"os"
+	"strings"
+
+	"github.com/devsy-org/devsy/e2e/framework"
+	"github.com/onsi/ginkgo/v2"
+	"github.com/onsi/gomega"
+)
+
+var _ = ginkgo.Describe(
+	"testing up command for podman provider",
+	ginkgo.Label("up-provider-podman-rootless-exec"),
+	func() {
+		var initialDir string
+
+		ginkgo.BeforeEach(func() {
+			var err error
+			initialDir, err = os.Getwd()
+			framework.ExpectNoError(err)
+		})
+
+		ginkgo.Context("with rootless podman", func() {
+			var f *framework.Framework
+
+			ginkgo.BeforeEach(func(ctx context.Context) {
+				var err error
+				f, err = setupDockerProvider(initialDir+"/bin", "podman")
+				framework.ExpectNoError(err)
+			})
+
+			ginkgo.Context("agent delivery", func() {
+				ginkgo.It(
+					"should deliver the agent binary and execute SSH commands",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace("tests/up/testdata/docker", initialDir, f)
+						framework.ExpectNoError(err)
+
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+
+						err = f.DevsySSHEchoTestString(ctx, tempDir)
+						framework.ExpectNoError(err)
+					},
+					ginkgo.SpecTimeout(framework.TimeoutShort()),
+				)
+			})
+
+			ginkgo.Context("exec", func() {
+				ginkgo.It(
+					"should execute commands inside the container via SSH",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace("tests/up/testdata/docker", initialDir, f)
+						framework.ExpectNoError(err)
+
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+
+						out, err := f.DevsySSH(ctx, tempDir, "echo -n hello-podman")
+						framework.ExpectNoError(err)
+						framework.ExpectEqual(out, "hello-podman")
+
+						out, err = f.DevsySSH(ctx, tempDir, "pwd")
+						framework.ExpectNoError(err)
+						gomega.Expect(strings.TrimSpace(out)).NotTo(gomega.BeEmpty())
+					},
+					ginkgo.SpecTimeout(framework.TimeoutShort()),
+				)
+			})
+
+			ginkgo.Context("cleanup", func() {
+				ginkgo.It(
+					"should delete workspace and clean up resources",
+					func(ctx context.Context) {
+						tempDir, err := framework.CopyToTempDir("tests/up/testdata/docker")
+						framework.ExpectNoError(err)
+						ginkgo.DeferCleanup(framework.CleanupTempDir, initialDir, tempDir)
+
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+
+						_, err = f.FindWorkspace(ctx, tempDir)
+						framework.ExpectNoError(err)
+
+						err = f.DevsyWorkspaceDelete(ctx, tempDir)
+						framework.ExpectNoError(err)
+
+						_, err = f.FindWorkspace(ctx, tempDir)
+						framework.ExpectError(err)
+					},
+					ginkgo.SpecTimeout(framework.TimeoutShort()),
+				)
+			})
+		})
+	},
+)
diff --git a/pkg/driver/docker/lifecycle_test.go b/pkg/driver/docker/lifecycle_test.go
index 55169e206..a13942d6c 100644
--- a/pkg/driver/docker/lifecycle_test.go
+++ b/pkg/driver/docker/lifecycle_test.go
@@ -80,8 +80,8 @@ esac
 func withShortImageInspectPoll(t *testing.T) {
 	t.Helper()
 	origInterval, origTimeout := imageInspectPollInterval, imageInspectPollTimeout
-	imageInspectPollInterval = time.Millisecond
-	imageInspectPollTimeout = 20 * time.Millisecond
+	imageInspectPollInterval = 5 * time.Millisecond
+	imageInspectPollTimeout = 300 * time.Millisecond
 	t.Cleanup(func() {
 		imageInspectPollInterval, imageInspectPollTimeout = origInterval, origTimeout
 	})