diff --git a/cli/root_test.go b/cli/root_test.go
index 85863b656a2aa..58297f9403acd 100644
--- a/cli/root_test.go
+++ b/cli/root_test.go
@@ -31,7 +31,8 @@ var updateGoldenFiles = flag.Bool("update", false, "update .golden files")
 //nolint:tparallel,paralleltest // These test sets env vars.
 func TestCommandHelp(t *testing.T) {
 	commonEnv := map[string]string{
-		"CODER_CONFIG_DIR": "/tmp/coder-cli-test-config",
+		"HOME":             "~",
+		"CODER_CONFIG_DIR": "~/.config/coderv2",
 	}
 
 	type testCase struct {
@@ -48,7 +49,7 @@ func TestCommandHelp(t *testing.T) {
 			name: "coder server --help",
 			cmd:  []string{"server", "--help"},
 			env: map[string]string{
-				"CODER_CACHE_DIRECTORY": "/tmp/coder-cli-test-cache",
+				"CODER_CACHE_DIRECTORY": "~/.cache/coder",
 			},
 		},
 		{
@@ -104,11 +105,19 @@ ExtractCommandPathsLoop:
 
 			ctx, _ := testutil.Context(t)
 
+			tmpwd := "/"
+			if runtime.GOOS == "windows" {
+				tmpwd = "C:\\"
+			}
+			err := os.Chdir(tmpwd)
 			var buf bytes.Buffer
 			root, _ := clitest.New(t, tt.cmd...)
 			root.SetOut(&buf)
-			err := root.ExecuteContext(ctx)
+			assert.NoError(t, err)
+			err = root.ExecuteContext(ctx)
+			err2 := os.Chdir(wd)
 			require.NoError(t, err)
+			require.NoError(t, err2)
 
 			got := buf.Bytes()
 			// Remove CRLF newlines (Windows).
@@ -116,7 +125,7 @@ ExtractCommandPathsLoop:
 
 			// The `coder templates create --help` command prints the path
 			// to the working directory (--directory flag default value).
-			got = bytes.ReplaceAll(got, []byte(wd), []byte("/tmp/coder-cli-test-workdir"))
+			got = bytes.ReplaceAll(got, []byte(fmt.Sprintf("%q", tmpwd)), []byte("\"[current directory]\""))
 
 			gf := filepath.Join("testdata", strings.Replace(tt.name, " ", "_", -1)+".golden")
 			if *updateGoldenFiles {
diff --git a/cli/testdata/coder_--help.golden b/cli/testdata/coder_--help.golden
index aa6f82b6cba35..41c7a97978cfc 100644
--- a/cli/testdata/coder_--help.golden
+++ b/cli/testdata/coder_--help.golden
@@ -48,7 +48,7 @@ Workspace Commands:
 
 Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
   -h, --help                  help for coder
diff --git a/cli/testdata/coder_agent_--help.golden b/cli/testdata/coder_agent_--help.golden
index ec5e1ab8273f4..2577cd660ed80 100644
--- a/cli/testdata/coder_agent_--help.golden
+++ b/cli/testdata/coder_agent_--help.golden
@@ -13,7 +13,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_config-ssh_--help.golden b/cli/testdata/coder_config-ssh_--help.golden
index 00a85cea6421e..b088c8586bc5b 100644
--- a/cli/testdata/coder_config-ssh_--help.golden
+++ b/cli/testdata/coder_config-ssh_--help.golden
@@ -27,7 +27,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_create_--help.golden b/cli/testdata/coder_create_--help.golden
index 52aaff8d1a053..6be1ea35363e0 100644
--- a/cli/testdata/coder_create_--help.golden
+++ b/cli/testdata/coder_create_--help.golden
@@ -23,7 +23,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_delete_--help.golden b/cli/testdata/coder_delete_--help.golden
index f20dd64119f36..9b25a441eb247 100644
--- a/cli/testdata/coder_delete_--help.golden
+++ b/cli/testdata/coder_delete_--help.golden
@@ -14,7 +14,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_dotfiles_--help.golden b/cli/testdata/coder_dotfiles_--help.golden
index 171fd895df27d..4db2317705566 100644
--- a/cli/testdata/coder_dotfiles_--help.golden
+++ b/cli/testdata/coder_dotfiles_--help.golden
@@ -17,7 +17,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_list_--help.golden b/cli/testdata/coder_list_--help.golden
index bdfcaae539895..9dc78e7a685d7 100644
--- a/cli/testdata/coder_list_--help.golden
+++ b/cli/testdata/coder_list_--help.golden
@@ -16,7 +16,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_login_--help.golden b/cli/testdata/coder_login_--help.golden
index f32395925538f..cbec6869dfa06 100644
--- a/cli/testdata/coder_login_--help.golden
+++ b/cli/testdata/coder_login_--help.golden
@@ -20,7 +20,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_logout_--help.golden b/cli/testdata/coder_logout_--help.golden
index 26158557d024e..3714b020ea892 100644
--- a/cli/testdata/coder_logout_--help.golden
+++ b/cli/testdata/coder_logout_--help.golden
@@ -9,7 +9,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_port-forward_--help.golden b/cli/testdata/coder_port-forward_--help.golden
index b825512cf953d..a61f2cb109b32 100644
--- a/cli/testdata/coder_port-forward_--help.golden
+++ b/cli/testdata/coder_port-forward_--help.golden
@@ -35,7 +35,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_publickey_--help.golden b/cli/testdata/coder_publickey_--help.golden
index 7712d9a04855d..f8b8f169dec9f 100644
--- a/cli/testdata/coder_publickey_--help.golden
+++ b/cli/testdata/coder_publickey_--help.golden
@@ -14,7 +14,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_rename_--help.golden b/cli/testdata/coder_rename_--help.golden
index a5e5111b294dc..54bf48b302eb4 100644
--- a/cli/testdata/coder_rename_--help.golden
+++ b/cli/testdata/coder_rename_--help.golden
@@ -9,7 +9,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_reset-password_--help.golden b/cli/testdata/coder_reset-password_--help.golden
index f961be5bc41da..1a99639c5765e 100644
--- a/cli/testdata/coder_reset-password_--help.golden
+++ b/cli/testdata/coder_reset-password_--help.golden
@@ -10,7 +10,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_restart_--help.golden b/cli/testdata/coder_restart_--help.golden
index 3c3f77766889b..afea82201ce55 100644
--- a/cli/testdata/coder_restart_--help.golden
+++ b/cli/testdata/coder_restart_--help.golden
@@ -9,7 +9,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_scaletest_--help.golden b/cli/testdata/coder_scaletest_--help.golden
index 64f88810bdb89..8949adc8a5df0 100644
--- a/cli/testdata/coder_scaletest_--help.golden
+++ b/cli/testdata/coder_scaletest_--help.golden
@@ -14,7 +14,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_scaletest_cleanup_--help.golden b/cli/testdata/coder_scaletest_cleanup_--help.golden
index 189780c0bc77b..a0a05274f36dd 100644
--- a/cli/testdata/coder_scaletest_cleanup_--help.golden
+++ b/cli/testdata/coder_scaletest_cleanup_--help.golden
@@ -16,7 +16,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_scaletest_create-workspaces_--help.golden b/cli/testdata/coder_scaletest_create-workspaces_--help.golden
index 0a5fbdcccacf7..0c07f92735093 100644
--- a/cli/testdata/coder_scaletest_create-workspaces_--help.golden
+++ b/cli/testdata/coder_scaletest_create-workspaces_--help.golden
@@ -115,7 +115,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_schedule_--help.golden b/cli/testdata/coder_schedule_--help.golden
index d29ef260e66f9..9018e6a2dede3 100644
--- a/cli/testdata/coder_schedule_--help.golden
+++ b/cli/testdata/coder_schedule_--help.golden
@@ -16,7 +16,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_schedule_override-stop_--help.golden b/cli/testdata/coder_schedule_override-stop_--help.golden
index 0ec9897b6e3da..8e5827e4fe129 100644
--- a/cli/testdata/coder_schedule_override-stop_--help.golden
+++ b/cli/testdata/coder_schedule_override-stop_--help.golden
@@ -14,7 +14,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_schedule_show_--help.golden b/cli/testdata/coder_schedule_show_--help.golden
index 86e65ff537bd9..3c2f4aba6e4e4 100644
--- a/cli/testdata/coder_schedule_show_--help.golden
+++ b/cli/testdata/coder_schedule_show_--help.golden
@@ -12,7 +12,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_schedule_start_--help.golden b/cli/testdata/coder_schedule_start_--help.golden
index 0dd02ba1a3720..1a2c137d42571 100644
--- a/cli/testdata/coder_schedule_start_--help.golden
+++ b/cli/testdata/coder_schedule_start_--help.golden
@@ -21,7 +21,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_schedule_stop_--help.golden b/cli/testdata/coder_schedule_stop_--help.golden
index bea7a4868f126..f5fad8ebd933c 100644
--- a/cli/testdata/coder_schedule_stop_--help.golden
+++ b/cli/testdata/coder_schedule_stop_--help.golden
@@ -22,7 +22,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_server_--help.golden b/cli/testdata/coder_server_--help.golden
index 294844255db94..2cc3ca502f1e2 100644
--- a/cli/testdata/coder_server_--help.golden
+++ b/cli/testdata/coder_server_--help.golden
@@ -28,7 +28,7 @@ Flags:
                                                      set, it will be used for compatibility
                                                      with systemd.
                                                      Consumes $CODER_CACHE_DIRECTORY (default
-                                                     "/tmp/coder-cli-test-cache")
+                                                     "~/.cache/coder")
       --dangerous-allow-path-app-sharing             Allow workspace apps that are not served
                                                      from subdomains to be shared. Path-based
                                                      app sharing is DISABLED by default for
@@ -307,7 +307,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_server_postgres-builtin-serve_--help.golden b/cli/testdata/coder_server_postgres-builtin-serve_--help.golden
index 3783656fb6c58..1bc7fd2fce7dc 100644
--- a/cli/testdata/coder_server_postgres-builtin-serve_--help.golden
+++ b/cli/testdata/coder_server_postgres-builtin-serve_--help.golden
@@ -9,7 +9,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_server_postgres-builtin-url_--help.golden b/cli/testdata/coder_server_postgres-builtin-url_--help.golden
index dafbff33ea737..6fe19269dc8fa 100644
--- a/cli/testdata/coder_server_postgres-builtin-url_--help.golden
+++ b/cli/testdata/coder_server_postgres-builtin-url_--help.golden
@@ -9,7 +9,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_show_--help.golden b/cli/testdata/coder_show_--help.golden
index bfa4b19c03e5e..2f4f68c0d254c 100644
--- a/cli/testdata/coder_show_--help.golden
+++ b/cli/testdata/coder_show_--help.golden
@@ -8,7 +8,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_speedtest_--help.golden b/cli/testdata/coder_speedtest_--help.golden
index 2697e4f6f3c90..fa8cb952a866c 100644
--- a/cli/testdata/coder_speedtest_--help.golden
+++ b/cli/testdata/coder_speedtest_--help.golden
@@ -12,7 +12,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_ssh_--help.golden b/cli/testdata/coder_ssh_--help.golden
index 4a716fa5eda62..20f5673b7de4a 100644
--- a/cli/testdata/coder_ssh_--help.golden
+++ b/cli/testdata/coder_ssh_--help.golden
@@ -36,7 +36,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_start_--help.golden b/cli/testdata/coder_start_--help.golden
index 32fab8f28ce4a..ced86097073c6 100644
--- a/cli/testdata/coder_start_--help.golden
+++ b/cli/testdata/coder_start_--help.golden
@@ -9,7 +9,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_state_--help.golden b/cli/testdata/coder_state_--help.golden
index 106dca76212a4..af5833729ddd1 100644
--- a/cli/testdata/coder_state_--help.golden
+++ b/cli/testdata/coder_state_--help.golden
@@ -14,7 +14,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_state_pull_--help.golden b/cli/testdata/coder_state_pull_--help.golden
index 254db8d328918..dcb7c9916e0d4 100644
--- a/cli/testdata/coder_state_pull_--help.golden
+++ b/cli/testdata/coder_state_pull_--help.golden
@@ -7,7 +7,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_state_push_--help.golden b/cli/testdata/coder_state_push_--help.golden
index 273bbf8575e61..bb5a2c9a78367 100644
--- a/cli/testdata/coder_state_push_--help.golden
+++ b/cli/testdata/coder_state_push_--help.golden
@@ -7,7 +7,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_stop_--help.golden b/cli/testdata/coder_stop_--help.golden
index 6cec091340b3c..63fe36c9d306c 100644
--- a/cli/testdata/coder_stop_--help.golden
+++ b/cli/testdata/coder_stop_--help.golden
@@ -9,7 +9,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_templates_--help.golden b/cli/testdata/coder_templates_--help.golden
index f014b33100fcd..cdbb0cda2ec15 100644
--- a/cli/testdata/coder_templates_--help.golden
+++ b/cli/testdata/coder_templates_--help.golden
@@ -37,7 +37,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_templates_create_--help.golden b/cli/testdata/coder_templates_create_--help.golden
index aebabdd55d1f5..0ca9259692326 100644
--- a/cli/testdata/coder_templates_create_--help.golden
+++ b/cli/testdata/coder_templates_create_--help.golden
@@ -7,7 +7,7 @@ Flags:
       --default-ttl duration          Specify a default TTL for workspaces created from this
                                       template. (default 24h0m0s)
   -d, --directory string              Specify the directory to create from, use '-' to read
-                                      tar from stdin (default "/tmp/coder-cli-test-workdir")
+                                      tar from stdin (default "[current directory]")
   -h, --help                          help for create
       --parameter-file string         Specify a file path with parameter values.
       --provisioner-tag stringArray   Specify a set of tags to target provisioner daemons.
@@ -15,7 +15,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_templates_delete_--help.golden b/cli/testdata/coder_templates_delete_--help.golden
index efa48abe90a87..9284d713bc2d2 100644
--- a/cli/testdata/coder_templates_delete_--help.golden
+++ b/cli/testdata/coder_templates_delete_--help.golden
@@ -9,7 +9,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_templates_edit_--help.golden b/cli/testdata/coder_templates_edit_--help.golden
index d5fbc8b92d72a..f92ba830ad7c6 100644
--- a/cli/testdata/coder_templates_edit_--help.golden
+++ b/cli/testdata/coder_templates_edit_--help.golden
@@ -17,7 +17,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_templates_init_--help.golden b/cli/testdata/coder_templates_init_--help.golden
index 8e273f5b8d331..076c5f0951a2f 100644
--- a/cli/testdata/coder_templates_init_--help.golden
+++ b/cli/testdata/coder_templates_init_--help.golden
@@ -8,7 +8,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_templates_list_--help.golden b/cli/testdata/coder_templates_list_--help.golden
index 113da8084892d..41cdd9eba3960 100644
--- a/cli/testdata/coder_templates_list_--help.golden
+++ b/cli/testdata/coder_templates_list_--help.golden
@@ -13,7 +13,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_templates_plan_--help.golden b/cli/testdata/coder_templates_plan_--help.golden
index 0c683ef7c8af9..fd3ca2e12eb39 100644
--- a/cli/testdata/coder_templates_plan_--help.golden
+++ b/cli/testdata/coder_templates_plan_--help.golden
@@ -8,7 +8,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_templates_pull_--help.golden b/cli/testdata/coder_templates_pull_--help.golden
index 3f2c869784b0a..af214b70ed954 100644
--- a/cli/testdata/coder_templates_pull_--help.golden
+++ b/cli/testdata/coder_templates_pull_--help.golden
@@ -9,7 +9,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_templates_push_--help.golden b/cli/testdata/coder_templates_push_--help.golden
index baf55609e7f17..a8a9653f446c1 100644
--- a/cli/testdata/coder_templates_push_--help.golden
+++ b/cli/testdata/coder_templates_push_--help.golden
@@ -7,7 +7,7 @@ Flags:
       --always-prompt                 Always prompt all parameters. Does not pull parameter
                                       values from active template version
   -d, --directory string              Specify the directory to create from, use '-' to read
-                                      tar from stdin (default "/tmp/coder-cli-test-workdir")
+                                      tar from stdin (default "[current directory]")
   -h, --help                          help for push
       --name string                   Specify a name for the new template version. It will be
                                       automatically generated if not provided.
@@ -17,7 +17,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_templates_versions_--help.golden b/cli/testdata/coder_templates_versions_--help.golden
index 28c3bf76c317f..b5b345ece283a 100644
--- a/cli/testdata/coder_templates_versions_--help.golden
+++ b/cli/testdata/coder_templates_versions_--help.golden
@@ -21,7 +21,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_templates_versions_list_--help.golden b/cli/testdata/coder_templates_versions_list_--help.golden
index 23edfca5e1b28..6d9844d0fc629 100644
--- a/cli/testdata/coder_templates_versions_list_--help.golden
+++ b/cli/testdata/coder_templates_versions_list_--help.golden
@@ -8,7 +8,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_tokens_--help.golden b/cli/testdata/coder_tokens_--help.golden
index cb5a824b84a24..66b068ebc180b 100644
--- a/cli/testdata/coder_tokens_--help.golden
+++ b/cli/testdata/coder_tokens_--help.golden
@@ -31,7 +31,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_tokens_create_--help.golden b/cli/testdata/coder_tokens_create_--help.golden
index 5cf5081f28dad..22cac73e41b95 100644
--- a/cli/testdata/coder_tokens_create_--help.golden
+++ b/cli/testdata/coder_tokens_create_--help.golden
@@ -10,7 +10,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_tokens_list_--help.golden b/cli/testdata/coder_tokens_list_--help.golden
index 92b22430f82a7..cf72c1c8f15c8 100644
--- a/cli/testdata/coder_tokens_list_--help.golden
+++ b/cli/testdata/coder_tokens_list_--help.golden
@@ -11,7 +11,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_tokens_remove_--help.golden b/cli/testdata/coder_tokens_remove_--help.golden
index 03c361efb1ff7..a0d46d2321b67 100644
--- a/cli/testdata/coder_tokens_remove_--help.golden
+++ b/cli/testdata/coder_tokens_remove_--help.golden
@@ -11,7 +11,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_update_--help.golden b/cli/testdata/coder_update_--help.golden
index 3f037ec8348e8..85ae220fdd5c1 100644
--- a/cli/testdata/coder_update_--help.golden
+++ b/cli/testdata/coder_update_--help.golden
@@ -15,7 +15,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_users_--help.golden b/cli/testdata/coder_users_--help.golden
index 21b3afb126556..c9b0b41d27405 100644
--- a/cli/testdata/coder_users_--help.golden
+++ b/cli/testdata/coder_users_--help.golden
@@ -20,7 +20,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_users_activate_--help.golden b/cli/testdata/coder_users_activate_--help.golden
index 67604e8cd82c4..895aeadab5727 100644
--- a/cli/testdata/coder_users_activate_--help.golden
+++ b/cli/testdata/coder_users_activate_--help.golden
@@ -16,7 +16,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_users_create_--help.golden b/cli/testdata/coder_users_create_--help.golden
index 3266f83f55300..ea1af046b1b25 100644
--- a/cli/testdata/coder_users_create_--help.golden
+++ b/cli/testdata/coder_users_create_--help.golden
@@ -9,7 +9,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_users_list_--help.golden b/cli/testdata/coder_users_list_--help.golden
index 9574e11d0b5c8..0ddb048a665aa 100644
--- a/cli/testdata/coder_users_list_--help.golden
+++ b/cli/testdata/coder_users_list_--help.golden
@@ -13,7 +13,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_users_show_--help.golden b/cli/testdata/coder_users_show_--help.golden
index 1cac8edce7268..250223390ba9c 100644
--- a/cli/testdata/coder_users_show_--help.golden
+++ b/cli/testdata/coder_users_show_--help.golden
@@ -12,7 +12,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_users_suspend_--help.golden b/cli/testdata/coder_users_suspend_--help.golden
index b0b949b41c05e..3e411849c2bc5 100644
--- a/cli/testdata/coder_users_suspend_--help.golden
+++ b/cli/testdata/coder_users_suspend_--help.golden
@@ -16,7 +16,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.
diff --git a/cli/testdata/coder_version_--help.golden b/cli/testdata/coder_version_--help.golden
index 722544319d5b6..c560938c09136 100644
--- a/cli/testdata/coder_version_--help.golden
+++ b/cli/testdata/coder_version_--help.golden
@@ -8,7 +8,7 @@ Flags:
 
 Global Flags:
       --global-config coder   Path to the global coder config directory.
-                              Consumes $CODER_CONFIG_DIR (default "/tmp/coder-cli-test-config")
+                              Consumes $CODER_CONFIG_DIR (default "~/.config/coderv2")
       --header stringArray    HTTP headers added to all requests. Provide as "Key=Value".
                               Consumes $CODER_HEADER
       --no-feature-warning    Suppress warnings about unlicensed features.