diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 390c843b0c9..60c4b5d1d4e 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -27628,27 +27628,19 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             case "console":
                 return Diagnostics.Cannot_find_name_0_Do_you_need_to_change_your_target_library_Try_changing_the_lib_compiler_option_to_include_dom;
             case "$":
-                return compilerOptions.types
-                    ? Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_jQuery_Try_npm_i_save_dev_types_Slashjquery_and_then_add_jquery_to_the_types_field_in_your_tsconfig
-                    : Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_jQuery_Try_npm_i_save_dev_types_Slashjquery;
+                return Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_jQuery_Try_npm_i_save_dev_types_Slashjquery_and_then_add_jquery_to_the_types_field_in_your_tsconfig;
             case "describe":
             case "suite":
             case "it":
             case "test":
-                return compilerOptions.types
-                    ? Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_a_test_runner_Try_npm_i_save_dev_types_Slashjest_or_npm_i_save_dev_types_Slashmocha_and_then_add_jest_or_mocha_to_the_types_field_in_your_tsconfig
-                    : Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_a_test_runner_Try_npm_i_save_dev_types_Slashjest_or_npm_i_save_dev_types_Slashmocha;
+                return Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_a_test_runner_Try_npm_i_save_dev_types_Slashjest_or_npm_i_save_dev_types_Slashmocha_and_then_add_jest_or_mocha_to_the_types_field_in_your_tsconfig;
             case "process":
             case "require":
             case "Buffer":
             case "module":
-                return compilerOptions.types
-                    ? Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_node_Try_npm_i_save_dev_types_Slashnode_and_then_add_node_to_the_types_field_in_your_tsconfig
-                    : Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_node_Try_npm_i_save_dev_types_Slashnode;
+                return Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_node_Try_npm_i_save_dev_types_Slashnode_and_then_add_node_to_the_types_field_in_your_tsconfig;
             case "Bun":
-                return compilerOptions.types
-                    ? Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_Bun_Try_npm_i_save_dev_types_Slashbun_and_then_add_bun_to_the_types_field_in_your_tsconfig
-                    : Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_Bun_Try_npm_i_save_dev_types_Slashbun;
+                return Diagnostics.Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_Bun_Try_npm_i_save_dev_types_Slashbun_and_then_add_bun_to_the_types_field_in_your_tsconfig;
             case "Map":
             case "Set":
             case "Promise":
diff --git a/src/compiler/programDiagnostics.ts b/src/compiler/programDiagnostics.ts
index ee4d1161eaa..45adc9ca756 100644
--- a/src/compiler/programDiagnostics.ts
+++ b/src/compiler/programDiagnostics.ts
@@ -400,7 +400,6 @@ export function createProgramDiagnostics(getCompilerOptionsObjectLiteralSyntax:
                     ) :
                     undefined;
             case FileIncludeKind.AutomaticTypeDirectiveFile:
-                if (!options.types) return undefined;
                 configFileNode = getOptionsSyntaxByArrayElementValue(getCompilerOptionsObjectLiteralSyntax(), "types", reason.typeReference);
                 message = Diagnostics.File_is_entry_point_of_type_library_specified_here;
                 break;
diff --git a/src/compiler/resolutionCache.ts b/src/compiler/resolutionCache.ts
index 6f1fc390723..4545b880907 100644
--- a/src/compiler/resolutionCache.ts
+++ b/src/compiler/resolutionCache.ts
@@ -1667,7 +1667,7 @@ export function createResolutionCache(resolutionHost: ResolutionCacheHost, rootD
      */
     function updateTypeRootsWatch() {
         const options = resolutionHost.getCompilationSettings();
-        if (options.types) {
+        if (options.types && !options.types.includes("*")) {
             // No need to do any watch since resolution cache is going to handle the failed lookups
             // for the types added by this
             closeTypeRootsWatch();
diff --git a/src/compiler/watch.ts b/src/compiler/watch.ts
index 4a49afdc364..19ba279f011 100644
--- a/src/compiler/watch.ts
+++ b/src/compiler/watch.ts
@@ -529,13 +529,9 @@ export function fileIncludeReasonToDiagnostics(program: Program, reason: FileInc
                 options.outFile ? "--outFile" : "--out",
             );
         case FileIncludeKind.AutomaticTypeDirectiveFile: {
-            const messageAndArgs: DiagnosticAndArguments = options.types ?
-                reason.packageId ?
-                    [Diagnostics.Entry_point_of_type_library_0_specified_in_compilerOptions_with_packageId_1, reason.typeReference, packageIdToString(reason.packageId)] :
-                    [Diagnostics.Entry_point_of_type_library_0_specified_in_compilerOptions, reason.typeReference] :
-                reason.packageId ?
-                [Diagnostics.Entry_point_for_implicit_type_library_0_with_packageId_1, reason.typeReference, packageIdToString(reason.packageId)] :
-                [Diagnostics.Entry_point_for_implicit_type_library_0, reason.typeReference];
+            const messageAndArgs: DiagnosticAndArguments = reason.packageId ?
+                [Diagnostics.Entry_point_of_type_library_0_specified_in_compilerOptions_with_packageId_1, reason.typeReference, packageIdToString(reason.packageId)] :
+                [Diagnostics.Entry_point_of_type_library_0_specified_in_compilerOptions, reason.typeReference];
 
             return chainDiagnosticMessages(/*details*/ undefined, ...messageAndArgs);
         }
diff --git a/src/jsTyping/jsTyping.ts b/src/jsTyping/jsTyping.ts
index 4554eb4c731..3153d329d10 100644
--- a/src/jsTyping/jsTyping.ts
+++ b/src/jsTyping/jsTyping.ts
@@ -133,7 +133,7 @@ export function discoverTypings(
     const exclude = typeAcquisition.exclude || [];
 
     // Directories to search for package.json, bower.json and other typing information
-    if (!compilerOptions.types) {
+    if (!compilerOptions.types || compilerOptions.types.includes("*")) {
         const possibleSearchDirs = new Set(fileNames.map(getDirectoryPath));
         possibleSearchDirs.add(projectRootPath);
         possibleSearchDirs.forEach(searchDir => {