diff --git a/pkg/machine/e2e/basic_test.go b/pkg/machine/e2e/basic_test.go
index 1f915528a7..63acf3710b 100644
--- a/pkg/machine/e2e/basic_test.go
+++ b/pkg/machine/e2e/basic_test.go
@@ -22,6 +22,7 @@ var _ = Describe("run basic podman commands", func() {
 		testDir, mb = setup()
 	})
 	AfterEach(func() {
+		dumpDebug(mb, testDir, CurrentSpecReport())
 		teardown(originalHomeDir, testDir, mb)
 	})
 
diff --git a/pkg/machine/e2e/info_test.go b/pkg/machine/e2e/info_test.go
index b016e3e1e1..dec494b6e9 100644
--- a/pkg/machine/e2e/info_test.go
+++ b/pkg/machine/e2e/info_test.go
@@ -20,6 +20,7 @@ var _ = Describe("podman machine info", func() {
 		testDir, mb = setup()
 	})
 	AfterEach(func() {
+		dumpDebug(mb, testDir, CurrentSpecReport())
 		teardown(originalHomeDir, testDir, mb)
 	})
 
diff --git a/pkg/machine/e2e/init_test.go b/pkg/machine/e2e/init_test.go
index 4aab924466..2023a0064e 100644
--- a/pkg/machine/e2e/init_test.go
+++ b/pkg/machine/e2e/init_test.go
@@ -27,6 +27,7 @@ var _ = Describe("podman machine init", func() {
 		testDir, mb = setup()
 	})
 	AfterEach(func() {
+		dumpDebug(mb, testDir, CurrentSpecReport())
 		teardown(originalHomeDir, testDir, mb)
 	})
 
diff --git a/pkg/machine/e2e/inspect_test.go b/pkg/machine/e2e/inspect_test.go
index 9645b42efb..6b3eb8c57b 100644
--- a/pkg/machine/e2e/inspect_test.go
+++ b/pkg/machine/e2e/inspect_test.go
@@ -19,6 +19,7 @@ var _ = Describe("podman inspect stop", func() {
 		testDir, mb = setup()
 	})
 	AfterEach(func() {
+		dumpDebug(mb, testDir, CurrentSpecReport())
 		teardown(originalHomeDir, testDir, mb)
 	})
 
diff --git a/pkg/machine/e2e/list_test.go b/pkg/machine/e2e/list_test.go
index 4cdef055e9..7063b22118 100644
--- a/pkg/machine/e2e/list_test.go
+++ b/pkg/machine/e2e/list_test.go
@@ -22,6 +22,7 @@ var _ = Describe("podman machine list", func() {
 		testDir, mb = setup()
 	})
 	AfterEach(func() {
+		dumpDebug(mb, testDir, CurrentSpecReport())
 		teardown(originalHomeDir, testDir, mb)
 	})
 
diff --git a/pkg/machine/e2e/machine_test.go b/pkg/machine/e2e/machine_test.go
index 5c2a0f30db..97794101f9 100644
--- a/pkg/machine/e2e/machine_test.go
+++ b/pkg/machine/e2e/machine_test.go
@@ -102,6 +102,11 @@ func setup() (string, *machineTestBuilder) {
 	if err := os.MkdirAll(filepath.Join(homeDir, ".ssh"), 0700); err != nil {
 		Fail(fmt.Sprintf("failed to create ssh dir: %q", err))
 	}
+	cConfDir := filepath.Join(homeDir, "containers")
+	if err := os.MkdirAll(cConfDir, 0755); err != nil {
+		Fail(fmt.Sprintf("failed to create %q: %s", cConfDir, err.Error()))
+	}
+
 	sshConfig, err := os.Create(filepath.Join(homeDir, ".ssh", "config"))
 	if err != nil {
 		Fail(fmt.Sprintf("failed to create ssh config: %q", err))
@@ -115,12 +120,44 @@ func setup() (string, *machineTestBuilder) {
 	if err := os.Setenv("HOME", homeDir); err != nil {
 		Fail("failed to set home dir")
 	}
+
+	fmt.Println("Set HOME to:", homeDir)
+	if err := os.Setenv("USERPROFILE", homeDir); err != nil {
+		Fail("failed to set USERPROFILE dir")
+	}
+
+	fmt.Println("Set USERPROFILE to:", homeDir)
+
 	if err := os.Setenv("XDG_RUNTIME_DIR", homeDir); err != nil {
-		Fail("failed to set xdg_runtime dir")
+		Fail("failed to set xdg_runtime_dir")
+	}
+
+	if err := os.Setenv("XDG_CONFIG_HOME", homeDir); err != nil {
+		Fail("failed to set xdg_CONFIG_HOME")
+	}
+
+	fmt.Println("Set XDG_CONFIG_HOME to ", homeDir)
+
+	cConf := filepath.Join(cConfDir, "containers.conf")
+	cc, err := os.Create(cConf)
+	if err != nil {
+		Fail("failed to create test container.conf")
+	}
+
+	if err := cc.Close(); err != nil {
+		Fail(fmt.Sprintf("unable to close file %q: %s", cConf, err.Error()))
 	}
+
+	if err := os.Setenv("CONTAINERS_CONF", cConf); err != nil {
+		Fail("failed to set CONTAINERS_CONF environment var")
+	}
+
+	fmt.Println("set CONTAINERS_CONF to ", cConf)
+
 	if err := os.Unsetenv("SSH_AUTH_SOCK"); err != nil {
 		Fail("unable to unset SSH_AUTH_SOCK")
 	}
+
 	mb, err := newMB()
 	if err != nil {
 		Fail(fmt.Sprintf("failed to create machine test: %q", err))
@@ -140,6 +177,7 @@ func setup() (string, *machineTestBuilder) {
 	if err := n.Close(); err != nil {
 		Fail(fmt.Sprintf("failed to close image copy handler: %q", err))
 	}
+
 	return homeDir, mb
 }
 
@@ -158,3 +196,18 @@ func teardown(origHomeDir string, testDir string, mb *machineTestBuilder) {
 		Fail("failed to set home dir")
 	}
 }
+
+// dumpDebug is called after each test and can be used to display useful debug information
+// about the environment
+func dumpDebug(mb *machineTestBuilder, testDir string, sr SpecReport) {
+	if !sr.Failed() {
+		return
+	}
+	fmt.Println("///////// DEBUG FOR FAILURE")
+	fmt.Println("test dir was: ", testDir)
+	debugMachine := basicMachine{}
+	// List connections
+	_, _ = mb.setCmd(debugMachine.withPodmanCommand([]string{"system", "connection", "ls"})).run()
+	// List machines
+	_, _ = mb.setCmd(debugMachine.withPodmanCommand([]string{"machine", "ls"})).run()
+}
diff --git a/pkg/machine/e2e/proxy_test.go b/pkg/machine/e2e/proxy_test.go
index 020fad5b0b..2d4e42353c 100644
--- a/pkg/machine/e2e/proxy_test.go
+++ b/pkg/machine/e2e/proxy_test.go
@@ -19,6 +19,7 @@ var _ = Describe("podman machine proxy settings propagation", func() {
 		testDir, mb = setup()
 	})
 	AfterEach(func() {
+		dumpDebug(mb, testDir, CurrentSpecReport())
 		teardown(originalHomeDir, testDir, mb)
 	})
 
diff --git a/pkg/machine/e2e/rm_test.go b/pkg/machine/e2e/rm_test.go
index 35f3f8cc2c..8b78438f83 100644
--- a/pkg/machine/e2e/rm_test.go
+++ b/pkg/machine/e2e/rm_test.go
@@ -20,6 +20,7 @@ var _ = Describe("podman machine rm", func() {
 		testDir, mb = setup()
 	})
 	AfterEach(func() {
+		dumpDebug(mb, testDir, CurrentSpecReport())
 		teardown(originalHomeDir, testDir, mb)
 	})
 
diff --git a/pkg/machine/e2e/set_test.go b/pkg/machine/e2e/set_test.go
index a7f7602d77..d9847fc8e6 100644
--- a/pkg/machine/e2e/set_test.go
+++ b/pkg/machine/e2e/set_test.go
@@ -22,6 +22,7 @@ var _ = Describe("podman machine set", func() {
 		testDir, mb = setup()
 	})
 	AfterEach(func() {
+		dumpDebug(mb, testDir, CurrentSpecReport())
 		teardown(originalHomeDir, testDir, mb)
 	})
 
diff --git a/pkg/machine/e2e/ssh_test.go b/pkg/machine/e2e/ssh_test.go
index 5fedfea0f7..abaf600232 100644
--- a/pkg/machine/e2e/ssh_test.go
+++ b/pkg/machine/e2e/ssh_test.go
@@ -17,6 +17,7 @@ var _ = Describe("podman machine ssh", func() {
 		testDir, mb = setup()
 	})
 	AfterEach(func() {
+		dumpDebug(mb, testDir, CurrentSpecReport())
 		teardown(originalHomeDir, testDir, mb)
 	})
 
diff --git a/pkg/machine/e2e/start_test.go b/pkg/machine/e2e/start_test.go
index d1001a45d2..b59dd4d7b8 100644
--- a/pkg/machine/e2e/start_test.go
+++ b/pkg/machine/e2e/start_test.go
@@ -16,6 +16,7 @@ var _ = Describe("podman machine start", func() {
 		testDir, mb = setup()
 	})
 	AfterEach(func() {
+		dumpDebug(mb, testDir, CurrentSpecReport())
 		teardown(originalHomeDir, testDir, mb)
 	})
 
diff --git a/pkg/machine/e2e/stop_test.go b/pkg/machine/e2e/stop_test.go
index 11c308e51b..22bd0c0f64 100644
--- a/pkg/machine/e2e/stop_test.go
+++ b/pkg/machine/e2e/stop_test.go
@@ -19,6 +19,7 @@ var _ = Describe("podman machine stop", func() {
 		testDir, mb = setup()
 	})
 	AfterEach(func() {
+		dumpDebug(mb, testDir, CurrentSpecReport())
 		teardown(originalHomeDir, testDir, mb)
 	})