diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 51c9493b61721..6bb09143260e8 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -19317,7 +19317,20 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                                     const symbolName = getFullyQualifiedName((indexType as UniqueESSymbolType).symbol, accessExpression);
                                     errorInfo = chainDiagnosticMessages(/*details*/ undefined, Diagnostics.Property_0_does_not_exist_on_type_1, "[" + symbolName + "]", typeToString(objectType));
                                 }
-                                else if (indexType.flags & TypeFlags.StringLiteral) {
+                                // Handle literals, type parameters (like K extends string), and keyof types
+                                else if (indexType.flags & (TypeFlags.StringLiteral | TypeFlags.TypeParameter | TypeFlags.Index)) {
+                                    // 1. Try specific property (only for literals)
+                                    if (indexType.flags & TypeFlags.StringLiteral) {
+                                        const prop = getPropertyOfType(objectType, escapeLeadingUnderscores((indexType as StringLiteralType).value));
+                                        if (prop) return getTypeOfSymbol(prop);
+                                    }
+
+                                    // 2. Fallback to string index signature for anything string-like
+                                    if (isTypeAssignableTo(indexType, stringType)) {
+                                        const indexInfo = getIndexInfoOfType(objectType, stringType);
+                                        if (indexInfo) return indexInfo.type;
+                                    }
+
                                     errorInfo = chainDiagnosticMessages(/*details*/ undefined, Diagnostics.Property_0_does_not_exist_on_type_1, (indexType as StringLiteralType).value, typeToString(objectType));
                                 }
                                 else if (indexType.flags & TypeFlags.NumberLiteral) {
diff --git a/tests/baselines/reference/stringLiteralIndexingWithIndexSignature.js b/tests/baselines/reference/stringLiteralIndexingWithIndexSignature.js
new file mode 100644
index 0000000000000..ef63bad5df276
--- /dev/null
+++ b/tests/baselines/reference/stringLiteralIndexingWithIndexSignature.js
@@ -0,0 +1,21 @@
+//// [tests/cases/compiler/stringLiteralIndexingWithIndexSignature.ts] ////
+
+//// [stringLiteralIndexingWithIndexSignature.ts]
+interface Dic<T> {
+    [key: string]: T;
+}
+
+function getVal<T, K extends string>(obj: Dic<T>, key: K) {
+    // This is the classic failure point for #30408
+    // It should resolve to 'T', but often resolves to 'any' or errors
+    return obj[key];
+}
+
+type Specific = Dic<number>["some_literal"]; // Should be 'number'
+
+//// [stringLiteralIndexingWithIndexSignature.js]
+function getVal(obj, key) {
+    // This is the classic failure point for #30408
+    // It should resolve to 'T', but often resolves to 'any' or errors
+    return obj[key];
+}
diff --git a/tests/baselines/reference/stringLiteralIndexingWithIndexSignature.symbols b/tests/baselines/reference/stringLiteralIndexingWithIndexSignature.symbols
new file mode 100644
index 0000000000000..2e7eda8120579
--- /dev/null
+++ b/tests/baselines/reference/stringLiteralIndexingWithIndexSignature.symbols
@@ -0,0 +1,33 @@
+//// [tests/cases/compiler/stringLiteralIndexingWithIndexSignature.ts] ////
+
+=== stringLiteralIndexingWithIndexSignature.ts ===
+interface Dic<T> {
+>Dic : Symbol(Dic, Decl(stringLiteralIndexingWithIndexSignature.ts, 0, 0))
+>T : Symbol(T, Decl(stringLiteralIndexingWithIndexSignature.ts, 0, 14))
+
+    [key: string]: T;
+>key : Symbol(key, Decl(stringLiteralIndexingWithIndexSignature.ts, 1, 5))
+>T : Symbol(T, Decl(stringLiteralIndexingWithIndexSignature.ts, 0, 14))
+}
+
+function getVal<T, K extends string>(obj: Dic<T>, key: K) {
+>getVal : Symbol(getVal, Decl(stringLiteralIndexingWithIndexSignature.ts, 2, 1))
+>T : Symbol(T, Decl(stringLiteralIndexingWithIndexSignature.ts, 4, 16))
+>K : Symbol(K, Decl(stringLiteralIndexingWithIndexSignature.ts, 4, 18))
+>obj : Symbol(obj, Decl(stringLiteralIndexingWithIndexSignature.ts, 4, 37))
+>Dic : Symbol(Dic, Decl(stringLiteralIndexingWithIndexSignature.ts, 0, 0))
+>T : Symbol(T, Decl(stringLiteralIndexingWithIndexSignature.ts, 4, 16))
+>key : Symbol(key, Decl(stringLiteralIndexingWithIndexSignature.ts, 4, 49))
+>K : Symbol(K, Decl(stringLiteralIndexingWithIndexSignature.ts, 4, 18))
+
+    // This is the classic failure point for #30408
+    // It should resolve to 'T', but often resolves to 'any' or errors
+    return obj[key];
+>obj : Symbol(obj, Decl(stringLiteralIndexingWithIndexSignature.ts, 4, 37))
+>key : Symbol(key, Decl(stringLiteralIndexingWithIndexSignature.ts, 4, 49))
+}
+
+type Specific = Dic<number>["some_literal"]; // Should be 'number'
+>Specific : Symbol(Specific, Decl(stringLiteralIndexingWithIndexSignature.ts, 8, 1))
+>Dic : Symbol(Dic, Decl(stringLiteralIndexingWithIndexSignature.ts, 0, 0))
+
diff --git a/tests/baselines/reference/stringLiteralIndexingWithIndexSignature.types b/tests/baselines/reference/stringLiteralIndexingWithIndexSignature.types
new file mode 100644
index 0000000000000..5a0684f4919b2
--- /dev/null
+++ b/tests/baselines/reference/stringLiteralIndexingWithIndexSignature.types
@@ -0,0 +1,32 @@
+//// [tests/cases/compiler/stringLiteralIndexingWithIndexSignature.ts] ////
+
+=== stringLiteralIndexingWithIndexSignature.ts ===
+interface Dic<T> {
+    [key: string]: T;
+>key : string
+>    : ^^^^^^
+}
+
+function getVal<T, K extends string>(obj: Dic<T>, key: K) {
+>getVal : <T, K extends string>(obj: Dic<T>, key: K) => T
+>       : ^ ^^ ^^^^^^^^^      ^^   ^^      ^^   ^^ ^^^^^^
+>obj : Dic<T>
+>    : ^^^^^^
+>key : K
+>    : ^
+
+    // This is the classic failure point for #30408
+    // It should resolve to 'T', but often resolves to 'any' or errors
+    return obj[key];
+>obj[key] : T
+>         : ^
+>obj : Dic<T>
+>    : ^^^^^^
+>key : K
+>    : ^
+}
+
+type Specific = Dic<number>["some_literal"]; // Should be 'number'
+>Specific : number
+>         : ^^^^^^
+
diff --git a/tests/cases/compiler/stringLiteralIndexingWithIndexSignature.ts b/tests/cases/compiler/stringLiteralIndexingWithIndexSignature.ts
new file mode 100644
index 0000000000000..f588e506559a6
--- /dev/null
+++ b/tests/cases/compiler/stringLiteralIndexingWithIndexSignature.ts
@@ -0,0 +1,12 @@
+// @noImplicitAny: true
+interface Dic<T> {
+    [key: string]: T;
+}
+
+function getVal<T, K extends string>(obj: Dic<T>, key: K) {
+    // This is the classic failure point for #30408
+    // It should resolve to 'T', but often resolves to 'any' or errors
+    return obj[key];
+}
+
+type Specific = Dic<number>["some_literal"]; // Should be 'number'
\ No newline at end of file