diff --git a/crates/pyrefly_config/src/config.rs b/crates/pyrefly_config/src/config.rs
index 9aab7f946a..2b8081a924 100644
--- a/crates/pyrefly_config/src/config.rs
+++ b/crates/pyrefly_config/src/config.rs
@@ -52,6 +52,8 @@ use pyrefly_util::telemetry::TelemetrySourceDbRebuildInstanceStats;
 use pyrefly_util::telemetry::TelemetrySourceDbRebuildStats;
 use pyrefly_util::watch_pattern::WatchPattern;
 use serde::Deserialize;
+use serde::de::SeqAccess;
+use serde::de::Visitor;
 use serde::Serialize;
 use starlark_map::small_map::SmallMap;
 use starlark_map::small_set::SmallSet;
@@ -79,15 +81,67 @@ pub static GENERATED_FILE_CONFIG_OVERRIDE: LazyLock<
 
 #[derive(Debug, PartialEq, Eq, Deserialize, Serialize, Clone)]
 pub struct SubConfig {
-    pub matches: Glob,
+    #[serde(alias = "match", deserialize_with = "deserialize_sub_config_matches")]
+    pub matches: Vec<Glob>,
     #[serde(flatten)]
     pub settings: ConfigBase,
 }
 
 impl SubConfig {
     fn rewrite_with_path_to_config(&mut self, config_root: &Path) {
-        self.matches = self.matches.clone().from_root(config_root);
+        self.matches = self
+            .matches
+            .clone()
+            .into_iter()
+            .map(|glob| glob.from_root(config_root))
+            .collect();
     }
+
+    fn matches_path(&self, path: &Path) -> bool {
+        self.matches.iter().any(|glob| glob.matches(path))
+    }
+}
+
+fn deserialize_sub_config_matches<'de, D>(deserializer: D) -> Result<Vec<Glob>, D::Error>
+where
+    D: serde::Deserializer<'de>,
+{
+    struct GlobListVisitor;
+
+    impl<'de> Visitor<'de> for GlobListVisitor {
+        type Value = Vec<Glob>;
+
+        fn expecting(&self, formatter: &mut fmt::Formatter) -> fmt::Result {
+            formatter.write_str("a glob string or an array of glob strings")
+        }
+
+        fn visit_string<E>(self, value: String) -> Result<Self::Value, E>
+        where
+            E: serde::de::Error,
+        {
+            Ok(vec![Glob::new(value).map_err(E::custom)?])
+        }
+
+        fn visit_str<E>(self, value: &str) -> Result<Self::Value, E>
+        where
+            E: serde::de::Error,
+        {
+            self.visit_string(value.to_owned())
+        }
+
+        fn visit_seq<A>(self, mut seq: A) -> Result<Self::Value, A::Error>
+        where
+            A: SeqAccess<'de>,
+        {
+            let mut matches = Vec::new();
+            while let Some(pattern) = seq.next_element::<Glob>()? {
+                matches.push(pattern);
+            }
+            Ok(matches)
+        }
+    }
+
+    deserializer.deserialize_any(GlobListVisitor)
 }
 
 /// Why a `ConfigFile` was synthesized rather than loaded from a real config
@@ -1007,7 +1061,7 @@ impl ConfigFile {
         path: &Path,
     ) -> Option<T> {
         self.sub_configs.iter().find_map(|c| {
-            if c.matches.matches(path) {
+            if c.matches_path(path) {
                 return getter(&c.settings);
             }
             None
@@ -1538,9 +1592,13 @@ impl ConfigFile {
             for sub_config in &config.sub_configs {
                 if !sub_config.settings.extras.0.is_empty() {
                     let extra_keys = sub_config.settings.extras.0.keys().join(", ");
+                    let matches = sub_config
+                        .matches
+                        .iter()
+                        .map(|glob| glob.to_string())
+                        .join(", ");
                     errors.push(ConfigError::warn(anyhow!(
-                        "Extra keys found in sub config matching {}: {extra_keys}",
-                        sub_config.matches
+                        "Extra keys found in sub config matching {matches}: {extra_keys}"
                     )));
                 }
             }
@@ -1729,7 +1787,7 @@ mod tests {
                 },
                 source_db: Default::default(),
                 sub_configs: vec![SubConfig {
-                    matches: Glob::new("sub/project/**".to_owned()).unwrap(),
+                    matches: vec![Glob::new("sub/project/**".to_owned()).unwrap()],
                     settings: ConfigBase {
                         extras: Default::default(),
                         errors: Some(ErrorDisplayConfig::new(HashMap::from_iter([
@@ -1822,7 +1880,7 @@ mod tests {
              python_platform = "windows"
 
              [[sub_config]]
-             matches = "abcd"
+             matches = ["abcd", "efgh"]
 
                  atliens = 1
                  "#;
@@ -1835,6 +1893,7 @@ mod tests {
             config.sub_configs[0].settings.extras.0,
             Table::from_iter([("atliens".to_owned(), Value::Integer(1))])
         );
+        assert_eq!(config.sub_configs[0].matches.len(), 2);
     }
 
     #[test]
@@ -1996,7 +2055,7 @@ mod tests {
             source_db: Default::default(),
             build_system: Default::default(),
             sub_configs: vec![SubConfig {
-                matches: Glob::new("sub/project/**".to_owned()).unwrap(),
+                matches: vec![Glob::new("sub/project/**".to_owned()).unwrap()],
                 settings: Default::default(),
             }],
             typeshed_path: Some(PathBuf::from(typeshed)),
@@ -2026,13 +2085,13 @@ mod tests {
         python_environment.site_package_path =
             Some(vec![test_path.join("venv/lib/python1.2.3/site-packages")]);
 
-        let sub_config_matches = Glob::new(
+        let sub_config_matches = vec![Glob::new(
             test_path
                 .join("sub/project/**")
                 .to_string_lossy()
                 .into_owned(),
         )
-        .unwrap();
+        .unwrap()];
 
         config.rewrite_with_path_to_config(&test_path);
 
@@ -2174,7 +2233,10 @@ output-format = "omit-errors"
             },
             sub_configs: vec![
                 SubConfig {
-                    matches: Glob::new("**/highest/**".to_owned()).unwrap(),
+                    matches: vec![
+                        Glob::new("**/highest/**".to_owned()).unwrap(),
+                        Glob::new("**/top/**".to_owned()).unwrap(),
+                    ],
                     settings: ConfigBase {
                         replace_imports_with_any: Some(vec![
                             ModuleWildcard::new("highest").unwrap(),
@@ -2184,7 +2246,7 @@ output-format = "omit-errors"
                     },
                 },
                 SubConfig {
-                    matches: Glob::new("**/priority*".to_owned()).unwrap(),
+                    matches: vec![Glob::new("**/priority*".to_owned()).unwrap()],
                     settings: ConfigBase {
                         replace_imports_with_any: Some(vec![
                             ModuleWildcard::new("second").unwrap(),
@@ -2203,6 +2265,11 @@ output-format = "omit-errors"
             ModuleName::from_str("highest")
         ));
 
+        assert!(config.replace_imports_with_any(
+            Some(Path::new("this/is/top/priority")),
+            ModuleName::from_str("highest")
+        ));
+
         // test find fallback match
         assert!(config.replace_imports_with_any(
             Some(Path::new("this/is/second/priority")),
@@ -2233,7 +2300,7 @@ output-format = "omit-errors"
                 ..Default::default()
             },
             sub_configs: vec![SubConfig {
-                matches: Glob::new("sub/**".to_owned()).unwrap(),
+                matches: vec![Glob::new("sub/**".to_owned()).unwrap()],
                 settings: ConfigBase {
                     errors: Some(ErrorDisplayConfig::new(HashMap::from([(
                         ErrorKind::BadReturn,
@@ -2282,7 +2349,7 @@ output-format = "omit-errors"
                 ..Default::default()
             },
             sub_configs: vec![SubConfig {
-                matches: Glob::new("strict/**".to_owned()).unwrap(),
+                matches: vec![Glob::new("strict/**".to_owned()).unwrap()],
                 settings: ConfigBase {
                     errors: Some(ErrorDisplayConfig::new(HashMap::from([(
                         ErrorKind::BadAssignment,
@@ -2314,7 +2381,7 @@ output-format = "omit-errors"
                 ..Default::default()
             },
             sub_configs: vec![SubConfig {
-                matches: Glob::new("sub/**".to_owned()).unwrap(),
+                matches: vec![Glob::new("sub/**".to_owned()).unwrap()],
                 settings: ConfigBase {
                     check_unannotated_defs: Some(false),
                     ..Default::default()
@@ -2616,7 +2683,7 @@ output-format = "omit-errors"
         let mut config = ConfigFile {
             preset: Some(Preset::Legacy),
             sub_configs: vec![SubConfig {
-                matches: Glob::new("tests/**".to_owned()).unwrap(),
+                matches: vec![Glob::new("tests/**".to_owned()).unwrap()],
                 settings: ConfigBase {
                     errors: Some(ErrorDisplayConfig::new(HashMap::from([(
                         ErrorKind::BadOverride,
diff --git a/crates/pyrefly_config/src/migration/pyright.rs b/crates/pyrefly_config/src/migration/pyright.rs
index 13135da486..497bbac497 100644
--- a/crates/pyrefly_config/src/migration/pyright.rs
+++ b/crates/pyrefly_config/src/migration/pyright.rs
@@ -40,7 +40,7 @@ impl ExecEnv {
             ..Default::default()
         };
         Ok(SubConfig {
-            matches: Glob::new(self.root)?,
+            matches: vec![Glob::new(self.root)?],
             settings,
         })
     }
diff --git a/crates/pyrefly_config/src/migration/sub_configs.rs b/crates/pyrefly_config/src/migration/sub_configs.rs
index a253ee21d0..d72bd1892f 100644
--- a/crates/pyrefly_config/src/migration/sub_configs.rs
+++ b/crates/pyrefly_config/src/migration/sub_configs.rs
@@ -59,24 +59,21 @@ impl ConfigOptionMigrater for SubConfigs {
 
         let sub_configs_vec = sub_configs
             .into_iter()
-            .flat_map(|(section, errors)| {
+            .map(|(section, errors)| -> anyhow::Result<SubConfig> {
                 // Split the section headers into individual modules and pair them with the section's error config.
                 // mypy uses module wildcards for its per-module sections, but we use globs.
                 // A simple translation: turn `.` into `/` and `*` into `**`, e.g. `a.*.b` -> `a/**/b`.
-                section
+                let matches = section
                     .split(",")
                     .map(|x| x.trim())
                     .filter(|x| !x.is_empty())
                     .map(|module| Glob::new(module.replace('.', "/").replace('*', "**")))
-                    .collect::<Vec<_>>()
-                    .into_iter()
-                    .zip(std::iter::repeat(Some(errors)))
-            })
-            .map(|(matches, errors)| -> anyhow::Result<SubConfig> {
+                    .collect::<Result<Vec<_>, _>>()?;
+
                 Ok(SubConfig {
-                    matches: matches?,
+                    matches,
                     settings: ConfigBase {
-                        errors,
+                        errors: Some(errors),
                         ..Default::default()
                     },
                 })
@@ -140,7 +137,7 @@ mod tests {
         assert_eq!(pyrefly_cfg.sub_configs.len(), 1);
 
         let sub_config = &pyrefly_cfg.sub_configs[0];
-        assert_eq!(sub_config.matches.to_string(), "app/models");
+        assert_eq!(sub_config.matches[0].to_string(), "app/models");
 
         let errors = sub_config.settings.errors.as_ref().unwrap();
         assert_eq!(
@@ -174,7 +171,7 @@ mod tests {
         let models_config = pyrefly_cfg
             .sub_configs
             .iter()
-            .find(|c| c.matches.to_string() == "app/models")
+            .find(|c| c.matches.iter().any(|glob| glob.to_string() == "app/models"))
             .unwrap();
         let models_errors = models_config.settings.errors.as_ref().unwrap();
         assert_eq!(
@@ -186,7 +183,7 @@ mod tests {
         let views_config = pyrefly_cfg
             .sub_configs
             .iter()
-            .find(|c| c.matches.to_string() == "app/views")
+            .find(|c| c.matches.iter().any(|glob| glob.to_string() == "app/views"))
             .unwrap();
         let views_errors = views_config.settings.errors.as_ref().unwrap();
         assert_eq!(
@@ -223,31 +220,26 @@ mod tests {
         let sub_configs = SubConfigs;
         let _ = sub_configs.migrate_from_mypy(&mypy_cfg, &mut pyrefly_cfg);
 
-        assert_eq!(pyrefly_cfg.sub_configs.len(), 2);
+        assert_eq!(pyrefly_cfg.sub_configs.len(), 1);
 
-        // Check that both modules have the same error config
+        // Check that both modules share the same error config in one sub-config.
         let models_config = pyrefly_cfg
             .sub_configs
             .iter()
-            .find(|c| c.matches.to_string() == "app/models")
+            .find(|c| c.matches.iter().any(|glob| glob.to_string() == "app/models"))
             .unwrap();
-        let views_config = pyrefly_cfg
-            .sub_configs
+
+        assert!(models_config
+            .matches
             .iter()
-            .find(|c| c.matches.to_string() == "app/views")
-            .unwrap();
+            .any(|glob| glob.to_string() == "app/views"));
 
         let models_errors = models_config.settings.errors.as_ref().unwrap();
-        let views_errors = views_config.settings.errors.as_ref().unwrap();
 
         assert_eq!(
             models_errors.severity(ErrorKind::MissingAttribute),
             Severity::Ignore
         );
-        assert_eq!(
-            views_errors.severity(ErrorKind::MissingAttribute),
-            Severity::Ignore
-        );
     }
 
     #[test]
@@ -268,7 +260,7 @@ mod tests {
 
         let sub_config = &pyrefly_cfg.sub_configs[0];
         // Check that the module wildcard was converted to a glob
-        assert_eq!(sub_config.matches.to_string(), "app/**/models");
+        assert_eq!(sub_config.matches[0].to_string(), "app/**/models");
 
         let errors = sub_config.settings.errors.as_ref().unwrap();
         assert_eq!(
@@ -325,14 +317,14 @@ mod tests {
         let src_config = pyrefly_cfg
             .sub_configs
             .iter()
-            .find(|c| c.matches.to_string() == "src")
+            .find(|c| c.matches.iter().any(|glob| glob.to_string() == "src"))
             .unwrap();
 
         // Find the sub_config for tests
         let tests_config = pyrefly_cfg
             .sub_configs
             .iter()
-            .find(|c| c.matches.to_string() == "tests")
+            .find(|c| c.matches.iter().any(|glob| glob.to_string() == "tests"))
             .unwrap();
 
         // Verify that the error settings were properly migrated
diff --git a/schemas/pyrefly.json b/schemas/pyrefly.json
index 8c4b51009b..4deaac350f 100644
--- a/schemas/pyrefly.json
+++ b/schemas/pyrefly.json
@@ -7,8 +7,18 @@
   "$defs": {
     "errorSeverity": {
       "oneOf": [
-        { "type": "boolean" },
-        { "type": "string", "enum": ["ignore", "info", "warn", "error"] }
+        {
+          "type": "boolean"
+        },
+        {
+          "type": "string",
+          "enum": [
+            "ignore",
+            "info",
+            "warn",
+            "error"
+          ]
+        }
       ]
     },
     "configBase": {
@@ -21,15 +31,33 @@
             "$ref": "#/$defs/errorSeverity"
           },
           "properties": {
-            "bad-assignment": { "$ref": "#/$defs/errorSeverity" },
-            "bad-return": { "$ref": "#/$defs/errorSeverity" },
-            "missing-import": { "$ref": "#/$defs/errorSeverity" },
-            "invalid-argument": { "$ref": "#/$defs/errorSeverity" },
-            "assert-type": { "$ref": "#/$defs/errorSeverity" },
-            "bad-override": { "$ref": "#/$defs/errorSeverity" },
-            "incompatible-type": { "$ref": "#/$defs/errorSeverity" },
-            "unused-import": { "$ref": "#/$defs/errorSeverity" },
-            "undefined-variable": { "$ref": "#/$defs/errorSeverity" }
+            "bad-assignment": {
+              "$ref": "#/$defs/errorSeverity"
+            },
+            "bad-return": {
+              "$ref": "#/$defs/errorSeverity"
+            },
+            "missing-import": {
+              "$ref": "#/$defs/errorSeverity"
+            },
+            "invalid-argument": {
+              "$ref": "#/$defs/errorSeverity"
+            },
+            "assert-type": {
+              "$ref": "#/$defs/errorSeverity"
+            },
+            "bad-override": {
+              "$ref": "#/$defs/errorSeverity"
+            },
+            "incompatible-type": {
+              "$ref": "#/$defs/errorSeverity"
+            },
+            "unused-import": {
+              "$ref": "#/$defs/errorSeverity"
+            },
+            "undefined-variable": {
+              "$ref": "#/$defs/errorSeverity"
+            }
           },
           "default": {}
         },
@@ -67,7 +95,11 @@
         "untyped-def-behavior": {
           "description": "How should Pyrefly treat function definitions with no parameter or return type annotations?",
           "type": "string",
-          "enum": ["check-and-infer-return-type", "check-and-infer-return-any", "skip-and-infer-return-any"],
+          "enum": [
+            "check-and-infer-return-type",
+            "check-and-infer-return-any",
+            "skip-and-infer-return-any"
+          ],
           "default": "check-and-infer-return-type"
         },
         "permissive-ignores": {
@@ -80,9 +112,19 @@
           "type": "array",
           "items": {
             "type": "string",
-            "enum": ["type", "pyrefly", "mypy", "pyright", "pyre", "ty"]
+            "enum": [
+              "type",
+              "pyrefly",
+              "mypy",
+              "pyright",
+              "pyre",
+              "ty"
+            ]
           },
-          "default": ["type", "pyrefly"]
+          "default": [
+            "type",
+            "pyrefly"
+          ]
         },
         "tensor-shapes": {
           "description": "Whether to enable tensor shape checking.",
@@ -96,7 +138,10 @@
         "recursion-overflow-handler": {
           "description": "How should Pyrefly handle recursion overflow during type evaluation?",
           "type": "string",
-          "enum": ["break-with-placeholder", "panic-with-debug-info"],
+          "enum": [
+            "break-with-placeholder",
+            "panic-with-debug-info"
+          ],
           "default": "break-with-placeholder"
         }
       }
@@ -112,7 +157,13 @@
         "preset": {
           "description": "Named preset that provides default error severities and behavior settings. User-specified settings override the preset.",
           "type": "string",
-          "enum": ["off", "basic", "legacy", "default", "strict"]
+          "enum": [
+            "off",
+            "basic",
+            "legacy",
+            "default",
+            "strict"
+          ]
         },
         "project-includes": {
           "description": "The glob patterns used to describe which files to type check, typically understood as user-space files. This does not specify import resolution priority.",
@@ -120,7 +171,10 @@
           "items": {
             "type": "string"
           },
-          "default": ["**/*.py*", "**/*.ipynb"]
+          "default": [
+            "**/*.py*",
+            "**/*.ipynb"
+          ]
         },
         "project-excludes": {
           "description": "The glob patterns used to describe which files to avoid type checking as a way to filter files that match project-includes.",
@@ -128,7 +182,12 @@
           "items": {
             "type": "string"
           },
-          "default": ["**/node_modules", "**/__pycache__", "**/venv/**", "**/.[!/.]*/**"]
+          "default": [
+            "**/node_modules",
+            "**/__pycache__",
+            "**/venv/**",
+            "**/.[!/.]*/**"
+          ]
         },
         "disable-project-excludes-heuristics": {
           "description": "Disable automatic appending of default project-excludes patterns. When true, you have full control over project-excludes.",
@@ -141,7 +200,9 @@
           "items": {
             "type": "string"
           },
-          "default": ["."]
+          "default": [
+            "."
+          ]
         },
         "disable-search-path-heuristics": {
           "description": "Disable any search path heuristics/additional search path behavior that Pyrefly will attempt to do for you.",
@@ -160,7 +221,16 @@
           "description": "The value used with conditions based on type checking against sys.platform values. Common values include 'linux', 'darwin', 'win32', but any valid sys.platform string is accepted.",
           "type": "string",
           "default": "linux",
-          "examples": ["linux", "darwin", "win32", "cygwin", "freebsd", "openbsd", "netbsd", "aix"]
+          "examples": [
+            "linux",
+            "darwin",
+            "win32",
+            "cygwin",
+            "freebsd",
+            "openbsd",
+            "netbsd",
+            "aix"
+          ]
         },
         "python-version": {
           "description": "The Python version to use for type checking. Format: <major>[.<minor>[.<micro>]]",
@@ -210,7 +280,10 @@
             "type": {
               "description": "The type of build system.",
               "type": "string",
-              "enum": ["buck", "custom"]
+              "enum": [
+                "buck",
+                "custom"
+              ]
             },
             "ignore-if-build-system-missing": {
               "description": "Whether to silently ignore the build system configuration if the build system is not found.",
@@ -249,32 +322,50 @@
               "type": "string"
             }
           },
-          "required": ["type"],
+          "required": [
+            "type"
+          ],
           "allOf": [
             {
               "if": {
                 "properties": {
-                  "type": {"const": "buck"}
+                  "type": {
+                    "const": "buck"
+                  }
                 }
               },
               "then": {
                 "not": {
-                  "required": ["command"]
+                  "required": [
+                    "command"
+                  ]
                 }
               }
             },
             {
               "if": {
                 "properties": {
-                  "type": {"const": "custom"}
+                  "type": {
+                    "const": "custom"
+                  }
                 }
               },
               "then": {
-                "required": ["command"],
+                "required": [
+                  "command"
+                ],
                 "not": {
                   "anyOf": [
-                    {"required": ["isolation-dir"]},
-                    {"required": ["extras"]}
+                    {
+                      "required": [
+                        "isolation-dir"
+                      ]
+                    },
+                    {
+                      "required": [
+                        "extras"
+                      ]
+                    }
                   ]
                 }
               }
@@ -291,11 +382,23 @@
               },
               {
                 "type": "object",
-                "required": ["matches"],
+                "required": [
+                  "matches"
+                ],
                 "properties": {
                   "matches": {
-                    "description": "A filesystem glob pattern detailing which files the config applies to.",
-                    "type": "string"
+                    "description": "One or more filesystem glob patterns detailing which files the config applies to.",
+                    "oneOf": [
+                      {
+                        "type": "string"
+                      },
+                      {
+                        "type": "array",
+                        "items": {
+                          "type": "string"
+                        }
+                      }
+                    ]
                   }
                 }
               }
@@ -307,4 +410,4 @@
     }
   ],
   "additionalProperties": true
-}
+}
\ No newline at end of file
diff --git a/schemas/test-pyproject.toml b/schemas/test-pyproject.toml
index bce4e79dfb..8a49fde813 100644
--- a/schemas/test-pyproject.toml
+++ b/schemas/test-pyproject.toml
@@ -6,42 +6,42 @@ version = "0.1.0"
 
 [tool.pyrefly]
 # Basic project configuration
-project-includes = ["src", "tests"]
-project-excludes = ["**/node_modules", "**/__pycache__"]
 disable-project-excludes-heuristics = false
+project-excludes = ["**/node_modules", "**/__pycache__"]
+project-includes = ["src", "tests"]
 
 # Import paths
-search-path = ["src", "lib"]
 disable-search-path-heuristics = false
+search-path = ["src", "lib"]
 site-package-path = ["venv/lib/python3.12/site-packages"]
 
 # Python environment
+conda-environment = "myenv"
+fallback-python-interpreter-name = "python3"
+python-interpreter-path = "venv/bin/python3"
 python-platform = "linux"
 python-version = "3.12.0"
 skip-interpreter-query = false
-python-interpreter-path = "venv/bin/python3"
-conda-environment = "myenv"
-fallback-python-interpreter-name = "python3"
 typeshed-path = "/path/to/typeshed"
 
 # Type checking behavior
-untyped-def-behavior = "check-and-infer-return-type"
-infer-with-first-use = true
-ignore-errors-in-generated-code = false
 disable-type-errors-in-ide = false
-tensor-shapes = false
-strict-callable-subtyping = false
+ignore-errors-in-generated-code = false
+infer-with-first-use = true
 recursion-depth-limit = 100
 recursion-overflow-handler = "break-with-placeholder"
+strict-callable-subtyping = false
+tensor-shapes = false
+untyped-def-behavior = "check-and-infer-return-type"
 
 # Import handling
-replace-imports-with-any = ["sympy.*", "*.series"]
 ignore-missing-imports = ["numpy.*"]
+replace-imports-with-any = ["sympy.*", "*.series"]
 
 # Ignore files and directives
-use-ignore-files = true
-permissive-ignores = false
 enabled-ignores = ["type", "pyrefly"]
+permissive-ignores = false
+use-ignore-files = true
 
 skip-lsp-config-indexing = false
 
@@ -52,12 +52,12 @@ baseline = "baseline.json"
 [tool.pyrefly.errors]
 bad-assignment = false
 bad-return = true
-missing-import = "warn"
 invalid-argument = "error"
+missing-import = "warn"
 
 # SubConfig example 1: Test files
 [[tool.pyrefly.sub-config]]
-matches = "**/tests/**"
+matches = ["**/tests/**", "**/tests/**/*.py"]
 untyped-def-behavior = "skip-and-infer-return-any"
 
 [tool.pyrefly.sub-config.errors]
@@ -65,14 +65,14 @@ assert-type = true
 
 # SubConfig example 2: Generated code
 [[tool.pyrefly.sub-config]]
-matches = "**/*_pb2.py"
 ignore-errors-in-generated-code = true
+matches = "**/*_pb2.py"
 replace-imports-with-any = ["google.protobuf.*"]
 
 # Build system configuration
 [tool.pyrefly.build-system]
-type = "buck"
-isolation-dir = "pyrefly-iso"
 extras = ["--config", "client.id=pyrefly"]
-search-path-prefix = ["/prefix"]
 ignore-if-build-system-missing = true
+isolation-dir = "pyrefly-iso"
+search-path-prefix = ["/prefix"]
+type = "buck"
diff --git a/schemas/test-pyrefly.toml b/schemas/test-pyrefly.toml
index 761f7f1f50..cdf75078ec 100644
--- a/schemas/test-pyrefly.toml
+++ b/schemas/test-pyrefly.toml
@@ -5,42 +5,42 @@
 preset = "legacy"
 
 # Basic project configuration
-project-includes = ["src", "tests"]
-project-excludes = ["**/node_modules", "**/__pycache__"]
 disable-project-excludes-heuristics = false
+project-excludes = ["**/node_modules", "**/__pycache__"]
+project-includes = ["src", "tests"]
 
 # Import paths
-search-path = ["src", "lib"]
 disable-search-path-heuristics = false
+search-path = ["src", "lib"]
 site-package-path = ["venv/lib/python3.12/site-packages"]
 
 # Python environment
+conda-environment = "myenv"
+fallback-python-interpreter-name = "python3"
+python-interpreter-path = "venv/bin/python3"
 python-platform = "linux"
 python-version = "3.12.0"
 skip-interpreter-query = false
-python-interpreter-path = "venv/bin/python3"
-conda-environment = "myenv"
-fallback-python-interpreter-name = "python3"
 typeshed-path = "/path/to/typeshed"
 
 # Type checking behavior
-untyped-def-behavior = "check-and-infer-return-type"
-infer-with-first-use = true
-ignore-errors-in-generated-code = false
 disable-type-errors-in-ide = false
-tensor-shapes = false
-strict-callable-subtyping = false
+ignore-errors-in-generated-code = false
+infer-with-first-use = true
 recursion-depth-limit = 100
 recursion-overflow-handler = "break-with-placeholder"
+strict-callable-subtyping = false
+tensor-shapes = false
+untyped-def-behavior = "check-and-infer-return-type"
 
 # Import handling
-replace-imports-with-any = ["sympy.*", "*.series"]
 ignore-missing-imports = ["numpy.*"]
+replace-imports-with-any = ["sympy.*", "*.series"]
 
 # Ignore files and directives
-use-ignore-files = true
-permissive-ignores = false
 enabled-ignores = ["type", "pyrefly"]
+permissive-ignores = false
+use-ignore-files = true
 
 skip-lsp-config-indexing = false
 
@@ -51,12 +51,12 @@ baseline = "baseline.json"
 [errors]
 bad-assignment = false
 bad-return = true
-missing-import = "warn"
 invalid-argument = "error"
+missing-import = "warn"
 
 # SubConfig example 1: Test files
 [[sub-config]]
-matches = "**/tests/**"
+matches = ["sub/project/tests/file.py", "sub/project/tests/**/*.py"]
 untyped-def-behavior = "skip-and-infer-return-any"
 
 [sub-config.errors]
@@ -64,14 +64,14 @@ assert-type = true
 
 # SubConfig example 2: Generated code
 [[sub-config]]
-matches = "**/*_pb2.py"
 ignore-errors-in-generated-code = true
+matches = "**/*_pb2.py"
 replace-imports-with-any = ["google.protobuf.*"]
 
 # Build system configuration
 [build-system]
-type = "buck"
-isolation-dir = "pyrefly-iso"
 extras = ["--config", "client.id=pyrefly"]
-search-path-prefix = ["/prefix"]
 ignore-if-build-system-missing = true
+isolation-dir = "pyrefly-iso"
+search-path-prefix = ["/prefix"]
+type = "buck"
diff --git a/website/docs/configuration.mdx b/website/docs/configuration.mdx
index a974fef386..b366029ab6 100644
--- a/website/docs/configuration.mdx
+++ b/website/docs/configuration.mdx
@@ -1159,7 +1159,7 @@ Examples:
 filepath glob matching. Only certain config options are allowed to be overridden, and a need
 to override other configs means you likely need to use a separate config file for your subdirectory.
 You can have as many SubConfigs as you want in a project, and even multiple separate SubConfigs
-that can apply to a given file when the `matches` glob pattern matches.
+that can apply to a given file when any `matches` glob pattern matches.
 
 #### **SubConfig Allowed Overrides**
 
@@ -1187,15 +1187,15 @@ and would like to see the option supported.
 
 A SubConfig has two or more entries:
 
-- a `matches` key, with a [Filesystem Glob](#filesystem-globbing) detailing which files the config
-  applies to.
+- a `matches` key, with a [Filesystem Glob](#filesystem-globbing) or list of globs detailing which
+  files the config applies to.
 - at least one of the [SubConfig allowed overrides](#subconfig-allowed-overrides)
 
 #### **SubConfig Option Selection**
 
 Since you can have more than one SubConfig matching a file, we need to define a resolution order
 to determine which SubConfig's option should be selected. Pyrefly does this by filtering
-SubConfigs whose `matches` does not match the given file, then takes the first non-null
+SubConfigs whose `matches` do not match the given file, then takes the first non-null
 value that can be found in the order the SubConfigs appear in your configuration.
 
 If no SubConfigs match, or there are no non-null config options present, then we take
@@ -1219,14 +1219,14 @@ invalid-argument = false
 
 [[sub-config]]
 # apply this to `sub/project/tests/file.py`
-matches = "sub/project/tests/file.py"
+matches = ["sub/project/tests/file.py", "sub/project/tests/**/*.py"]
 
 # any unittest imports will by typed as `typing.Any`
 replace-imports-with-any = ["unittest.*"]
 
 [[sub-config]]
 # apply this config to all files in `sub/project`
-matches = "sub/project/**"
+matches = ["sub/project/**", "sub/project/tests/**"]
 
 # enable `assert-type` errors in `sub/project`
 [sub-config.errors]
@@ -1234,7 +1234,7 @@ assert-type = true
 
 [[sub-config]]
 # apply this config to all files in `sub`
-matches = "sub/**"
+matches = ["sub/**", "sub/project/**"]
 
 # disable `assert-type` errors in `sub`
 [sub-config.errors]
@@ -1242,7 +1242,7 @@ assert-type = false
 
 [[sub-config]]
 # apply this config to all files under `tests` dirs in `sub/`
-matches = "sub/**/tests/**"
+matches = ["sub/**/tests/**", "sub/tests/**"]
 
 # any pytest imports will be typed as `typing.Any`
 replace-imports-with-any = ["pytest.*"]
@@ -1378,14 +1378,14 @@ invalid-argument = false
 
 [[sub-config]]
 # apply this to `sub/project/tests/file.py`
-matches = "sub/project/tests/file.py"
+matches = ["sub/project/tests/file.py", "sub/project/tests/**/*.py"]
 
 # any unittest imports will by typed as `typing.Any`
 replace-imports-with-any = ["unittest.*"]
 
 [[sub-config]]
 # apply this config to all files in `sub/project`
-matches = "sub/project/**"
+matches = ["sub/project/**", "sub/project/tests/**"]
 
 # enable `assert-type` errors in `sub/project`
 [sub-config.errors]
@@ -1425,7 +1425,7 @@ invalid-argument = false
 
 [[tool.pyrefly.sub-config]]
 # apply this config to all files in `sub/project`
-matches = "sub/project/**"
+matches = ["sub/project/**", "sub/project/tests/**"]
 
 # enable `assert-type` errors in `sub/project`
 [tool.pyrefly.sub-config.errors]
@@ -1433,7 +1433,7 @@ assert-type = true
 
 [[tool.pyrefly.sub-config]]
 # apply this config to all files in `sub`
-matches = "sub/**"
+matches = ["sub/**", "sub/project/**"]
 
 # disable `assert-type` errors in `sub/project`
 [tool.pyrefly.sub-config.errors]