diff --git a/commands/auth.go b/commands/auth.go
index fa2d3cd70..51fbe017a 100644
--- a/commands/auth.go
+++ b/commands/auth.go
@@ -353,13 +353,22 @@ func writeConfig() error {
 
 // defaultConfigFileWriter returns a writer to a newly created config.yaml file in the default config home.
 // When using the default config file path the default config home directory will be created; Otherwise
-// the custom config home directory must exist and be writable to the user issuing the auth command.
+// the custom config home directory will be created if it doesn't exist.
 func defaultConfigFileWriter() (io.WriteCloser, error) {
 	cfgFile := viper.GetString("config")
 
 	defaultCfgFile := filepath.Join(defaultConfigHome(), defaultConfigName)
 	if cfgFile == defaultCfgFile {
 		configHome()
+	} else {
+		// For custom config paths, ensure the parent directory exists
+		parentDir := filepath.Dir(cfgFile)
+		if _, err := os.Stat(parentDir); os.IsNotExist(err) {
+			err = os.MkdirAll(parentDir, 0755)
+			if err != nil {
+				return nil, err
+			}
+		}
 	}
 
 	f, err := os.Create(cfgFile)
diff --git a/commands/doit.go b/commands/doit.go
index ed583893a..3430b8352 100644
--- a/commands/doit.go
+++ b/commands/doit.go
@@ -149,8 +149,22 @@ func defaultConfigHome() string {
 
 func configHome() string {
 	ch := defaultConfigHome()
-	err := os.MkdirAll(ch, 0755)
-	checkErr(err)
+
+	// Get the parent directory to check if it exists
+	parentDir := filepath.Dir(ch)
+
+	// Check if parent directory exists (could be a symlink or directory)
+	if _, err := os.Stat(parentDir); os.IsNotExist(err) {
+		// Parent doesn't exist, create it with MkdirAll
+		err = os.MkdirAll(parentDir, 0755)
+		checkErr(err)
+	}
+
+	// Now create the final directory (doctl) if it doesn't exist
+	if _, err := os.Stat(ch); os.IsNotExist(err) {
+		err = os.Mkdir(ch, 0755)
+		checkErr(err)
+	}
 
 	return ch
 }
diff --git a/integration/auth_test.go b/integration/auth_test.go
index ab37f3fce..cc60f97cf 100644
--- a/integration/auth_test.go
+++ b/integration/auth_test.go
@@ -284,68 +284,51 @@ context: default
 			)
 
 			output, err := cmd.CombinedOutput()
-			expect.NoError(err, string(output))
-
-			err = os.Remove(testConfig)
 			expect.NoError(err)
+
+			expect.Contains(string(output), "next (current)")
 		})
 	})
 
-	when("switching contexts containing a period", func() {
-		it("does not mangle that context", func() {
-			var testConfigBytes = []byte(`access-token: first-token
-auth-contexts:
-  test@example.com: second-token
-context: default
-`)
-
+	when("config directory parent is a symlink", func() {
+		it("successfully creates config directory through symlink", func() {
 			tmpDir := t.TempDir()
-			testConfig := filepath.Join(tmpDir, "test-config.yml")
-			expect.NoError(os.WriteFile(testConfig, testConfigBytes, 0644))
 
-			cmd := exec.Command(builtBinaryPath,
-				"-u", server.URL,
-				"auth",
-				"switch",
-				"--config", testConfig,
-			)
-			_, err := cmd.CombinedOutput()
+			// Create actual config directory
+			actualConfigDir := filepath.Join(tmpDir, "actual-config")
+			err := os.MkdirAll(actualConfigDir, 0755)
 			expect.NoError(err)
 
-			fileBytes, err := os.ReadFile(testConfig)
+			// Create a symlink .config pointing to the actual config directory
+			symlinkConfigDir := filepath.Join(tmpDir, ".config")
+			err = os.Symlink(actualConfigDir, symlinkConfigDir)
 			expect.NoError(err)
-			expect.Contains(string(fileBytes), "test@example.com: second-token")
-
-			err = os.Remove(testConfig)
-			expect.NoError(err)
-		})
-	})
 
-	when("the DIGITALOCEAN_CONTEXT variable is set", func() {
-		it("uses that context for commands", func() {
-			var testConfigBytes = []byte(`access-token: first-token
-auth-contexts:
-  next: second-token
-context: default
-`)
-
-			tmpDir := t.TempDir()
-			testConfig := filepath.Join(tmpDir, "test-config.yml")
-			expect.NoError(os.WriteFile(testConfig, testConfigBytes, 0644))
+			// Set up config path to use the symlink
+			configPath := filepath.Join(symlinkConfigDir, "doctl", "config.yml")
 
 			cmd := exec.Command(builtBinaryPath,
 				"-u", server.URL,
+				"--config", configPath,
 				"auth",
-				"list",
-				"--config", testConfig,
+				"init",
+				"--access-token", "some-magic-token",
+				"--token-validation-server", server.URL,
 			)
-			cmd.Env = os.Environ()
-			cmd.Env = append(cmd.Env, "DIGITALOCEAN_CONTEXT=next")
 
-			output, err := cmd.CombinedOutput()
-			expect.NoError(err, string(output))
+			_, err = cmd.CombinedOutput()
+			expect.NoError(err)
 
-			expect.Contains(string(output), "next (current)")
+			// Verify the config file was created
+			fileBytes, err := os.ReadFile(configPath)
+			expect.NoError(err)
+			expect.Contains(string(fileBytes), "access-token: some-magic-token")
+
+			// Verify the directory structure exists through the symlink
+			doctlDir := filepath.Join(symlinkConfigDir, "doctl")
+			info, err := os.Stat(doctlDir)
+			expect.NoError(err)
+			expect.True(info.IsDir())
 		})
 	})
 })