diff --git a/e2e/tests/up/provider_podman.go b/e2e/tests/up/provider_podman.go
index f994696d6..b903c9cba 100644
--- a/e2e/tests/up/provider_podman.go
+++ b/e2e/tests/up/provider_podman.go
@@ -4,9 +4,11 @@ import (
 	"context"
 	"os"
 	"os/exec"
+	"strings"
 
 	"github.com/devsy-org/devsy/e2e/framework"
 	"github.com/onsi/ginkgo/v2"
+	"github.com/onsi/gomega"
 )
 
 var _ = ginkgo.Describe(
@@ -30,17 +32,142 @@ var _ = ginkgo.Describe(
 				framework.ExpectNoError(err)
 			})
 
-			ginkgo.It(
-				"should start a new workspace with existing image",
-				func(ctx context.Context) {
-					tempDir, err := setupWorkspace("tests/up/testdata/docker", initialDir, f)
-					framework.ExpectNoError(err)
+			ginkgo.Context("basic", func() {
+				ginkgo.It(
+					"should start a new workspace with existing image",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace("tests/up/testdata/docker", initialDir, f)
+						framework.ExpectNoError(err)
 
-					err = f.DevsyUp(ctx, tempDir)
-					framework.ExpectNoError(err)
-				},
-				ginkgo.SpecTimeout(framework.TimeoutShort()),
-			)
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+					},
+					ginkgo.SpecTimeout(framework.TimeoutShort()),
+				)
+			})
+
+			ginkgo.Context("build", func() {
+				ginkgo.It(
+					"should start a workspace with a multistage Dockerfile build",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace(
+							"tests/up/testdata/docker-with-multi-stage-build",
+							initialDir,
+							f,
+						)
+						framework.ExpectNoError(err)
+
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+					},
+					ginkgo.SpecTimeout(framework.TimeoutLong()),
+				)
+
+				ginkgo.It(
+					"should build and respect overrideCommand false",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace(
+							"tests/up/testdata/docker-override-command-false",
+							initialDir,
+							f,
+						)
+						framework.ExpectNoError(err)
+
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+					},
+					ginkgo.SpecTimeout(framework.TimeoutShort()),
+				)
+			})
+
+			ginkgo.Context("lifecycle commands", func() {
+				ginkgo.It(
+					"should run postCreateCommand with object syntax",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace(
+							"tests/up/testdata/docker-postcreate-parallel",
+							initialDir,
+							f,
+						)
+						framework.ExpectNoError(err)
+
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+
+						one, err := f.DevsySSH(ctx, tempDir, "cat /tmp/post-create-one.out")
+						framework.ExpectNoError(err)
+						gomega.Expect(strings.TrimSpace(one)).To(gomega.Equal("postCreateOne"))
+
+						two, err := f.DevsySSH(ctx, tempDir, "cat /tmp/post-create-two.out")
+						framework.ExpectNoError(err)
+						gomega.Expect(strings.TrimSpace(two)).To(gomega.Equal("postCreateTwo"))
+					},
+					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()),
+				)
+			})
 		})
 
 		ginkgo.Context("with rootful podman", func() {
@@ -59,7 +186,7 @@ var _ = ginkgo.Describe(
 				err = wrapper.Close()
 				framework.ExpectNoError(err)
 
-				// #nosec G302 -- TODO Consider using a more secure permission setting and ownership if needed.
+				// #nosec G302 -- wrapper script needs execute permission
 				err = os.Chmod(initialDir+"/bin/podman-rootful", 0o755)
 				framework.ExpectNoError(err)
 
@@ -74,17 +201,142 @@ var _ = ginkgo.Describe(
 				framework.ExpectNoError(err)
 			})
 
-			ginkgo.It(
-				"should start a new workspace with existing image",
-				func(ctx context.Context) {
-					tempDir, err := setupWorkspace("tests/up/testdata/docker", initialDir, f)
-					framework.ExpectNoError(err)
+			ginkgo.Context("basic", func() {
+				ginkgo.It(
+					"should start a new workspace with existing image",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace("tests/up/testdata/docker", initialDir, f)
+						framework.ExpectNoError(err)
 
-					err = f.DevsyUp(ctx, tempDir)
-					framework.ExpectNoError(err)
-				},
-				ginkgo.SpecTimeout(framework.TimeoutShort()),
-			)
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+					},
+					ginkgo.SpecTimeout(framework.TimeoutShort()),
+				)
+			})
+
+			ginkgo.Context("build", func() {
+				ginkgo.It(
+					"should start a workspace with a multistage Dockerfile build",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace(
+							"tests/up/testdata/docker-with-multi-stage-build",
+							initialDir,
+							f,
+						)
+						framework.ExpectNoError(err)
+
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+					},
+					ginkgo.SpecTimeout(framework.TimeoutLong()),
+				)
+
+				ginkgo.It(
+					"should build and respect overrideCommand false",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace(
+							"tests/up/testdata/docker-override-command-false",
+							initialDir,
+							f,
+						)
+						framework.ExpectNoError(err)
+
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+					},
+					ginkgo.SpecTimeout(framework.TimeoutShort()),
+				)
+			})
+
+			ginkgo.Context("lifecycle commands", func() {
+				ginkgo.It(
+					"should run postCreateCommand with object syntax",
+					func(ctx context.Context) {
+						tempDir, err := setupWorkspace(
+							"tests/up/testdata/docker-postcreate-parallel",
+							initialDir,
+							f,
+						)
+						framework.ExpectNoError(err)
+
+						err = f.DevsyUp(ctx, tempDir)
+						framework.ExpectNoError(err)
+
+						one, err := f.DevsySSH(ctx, tempDir, "cat /tmp/post-create-one.out")
+						framework.ExpectNoError(err)
+						gomega.Expect(strings.TrimSpace(one)).To(gomega.Equal("postCreateOne"))
+
+						two, err := f.DevsySSH(ctx, tempDir, "cat /tmp/post-create-two.out")
+						framework.ExpectNoError(err)
+						gomega.Expect(strings.TrimSpace(two)).To(gomega.Equal("postCreateTwo"))
+					},
+					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()),
+				)
+			})
 		})
 	},
 )