diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index dfa8c72d36645..44a3241045cc4 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -32810,7 +32810,7 @@ namespace ts {
                 case SyntaxKind.MinusToken:
                 case SyntaxKind.TildeToken:
                     checkNonNullType(operandType, node.operand);
-                    if (maybeTypeOfKind(operandType, TypeFlags.ESSymbolLike)) {
+                    if (maybeTypeOfKindConsideringBaseConstraint(operandType, TypeFlags.ESSymbolLike)) {
                         error(node.operand, Diagnostics.The_0_operator_cannot_be_applied_to_type_symbol, tokenToString(node.operator));
                     }
                     if (node.operator === SyntaxKind.PlusToken) {
@@ -32871,6 +32871,15 @@ namespace ts {
             return numberType;
         }
 
+        function maybeTypeOfKindConsideringBaseConstraint(type: Type, kind: TypeFlags): boolean {
+            if (maybeTypeOfKind(type, kind)) {
+                return true;
+            }
+
+            const baseConstraint = getBaseConstraintOrType(type);
+            return !!baseConstraint && maybeTypeOfKind(baseConstraint, kind);
+        }
+
         // Return true if type might be of the given kind. A union or intersection type might be of a given
         // kind if at least one constituent type is of the given kind.
         function maybeTypeOfKind(type: Type, kind: TypeFlags): boolean {
@@ -33654,8 +33663,8 @@ namespace ts {
             // Return true if there was no error, false if there was an error.
             function checkForDisallowedESSymbolOperand(operator: SyntaxKind): boolean {
                 const offendingSymbolOperand =
-                    maybeTypeOfKind(leftType, TypeFlags.ESSymbolLike) ? left :
-                    maybeTypeOfKind(rightType, TypeFlags.ESSymbolLike) ? right :
+                    maybeTypeOfKindConsideringBaseConstraint(leftType, TypeFlags.ESSymbolLike) ? left :
+                    maybeTypeOfKindConsideringBaseConstraint(rightType, TypeFlags.ESSymbolLike) ? right :
                     undefined;
 
                 if (offendingSymbolOperand) {
@@ -33893,7 +33902,7 @@ namespace ts {
             const types = [];
             for (const span of node.templateSpans) {
                 const type = checkExpression(span.expression);
-                if (maybeTypeOfKind(type, TypeFlags.ESSymbolLike)) {
+                if (maybeTypeOfKindConsideringBaseConstraint(type, TypeFlags.ESSymbolLike)) {
                     error(span.expression, Diagnostics.Implicit_conversion_of_a_symbol_to_a_string_will_fail_at_runtime_Consider_wrapping_this_expression_in_String);
                 }
                 texts.push(span.literal.text);
diff --git a/tests/baselines/reference/noImplicitSymbolToString.errors.txt b/tests/baselines/reference/noImplicitSymbolToString.errors.txt
index cb664d9a8b93e..b90cf982dd398 100644
--- a/tests/baselines/reference/noImplicitSymbolToString.errors.txt
+++ b/tests/baselines/reference/noImplicitSymbolToString.errors.txt
@@ -3,9 +3,19 @@ tests/cases/compiler/noImplicitSymbolToString.ts(7,30): error TS2469: The '+' op
 tests/cases/compiler/noImplicitSymbolToString.ts(8,8): error TS2469: The '+=' operator cannot be applied to type 'symbol'.
 tests/cases/compiler/noImplicitSymbolToString.ts(13,47): error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
 tests/cases/compiler/noImplicitSymbolToString.ts(13,90): error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
+tests/cases/compiler/noImplicitSymbolToString.ts(21,15): error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
+tests/cases/compiler/noImplicitSymbolToString.ts(26,8): error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
+tests/cases/compiler/noImplicitSymbolToString.ts(27,5): error TS2469: The '+' operator cannot be applied to type 'symbol'.
+tests/cases/compiler/noImplicitSymbolToString.ts(28,6): error TS2469: The '+' operator cannot be applied to type 'symbol'.
+tests/cases/compiler/noImplicitSymbolToString.ts(31,8): error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
+tests/cases/compiler/noImplicitSymbolToString.ts(32,5): error TS2469: The '+' operator cannot be applied to type 'symbol'.
+tests/cases/compiler/noImplicitSymbolToString.ts(33,6): error TS2469: The '+' operator cannot be applied to type 'symbol'.
+tests/cases/compiler/noImplicitSymbolToString.ts(43,8): error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
+tests/cases/compiler/noImplicitSymbolToString.ts(44,5): error TS2469: The '+' operator cannot be applied to type 'symbol'.
+tests/cases/compiler/noImplicitSymbolToString.ts(45,6): error TS2469: The '+' operator cannot be applied to type 'symbol'.
 
 
-==== tests/cases/compiler/noImplicitSymbolToString.ts (5 errors) ====
+==== tests/cases/compiler/noImplicitSymbolToString.ts (15 errors) ====
     // Fix #19666
     
     let symbol!: symbol;
@@ -29,4 +39,57 @@ tests/cases/compiler/noImplicitSymbolToString.ts(13,90): error TS2731: Implicit
 !!! error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
                                                                                              ~~~~~~~~~~~~~~~~~
 !!! error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
+    
+    
+    // Fix #44462
+    
+    type StringOrSymbol = string | symbol;
+    
+    function getKey<S extends StringOrSymbol>(key: S) {
+        return `${key} is the key`;
+                  ~~~
+!!! error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
+    }
+    
+    function getKey1<S extends symbol>(key: S) {
+        let s1!: S;
+        `${s1}`;
+           ~~
+!!! error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
+        s1 + '';
+        ~~
+!!! error TS2469: The '+' operator cannot be applied to type 'symbol'.
+        +s1;
+         ~~
+!!! error TS2469: The '+' operator cannot be applied to type 'symbol'.
+    
+        let s2!: S | string;
+        `${s2}`;
+           ~~
+!!! error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
+        s2 + '';
+        ~~
+!!! error TS2469: The '+' operator cannot be applied to type 'symbol'.
+        +s2;
+         ~~
+!!! error TS2469: The '+' operator cannot be applied to type 'symbol'.
+    }
+    
+    function getKey2<S extends string>(key: S) {
+        let s1!: S;
+        `${s1}`;
+        s1 + '';
+        +s1;
+    
+        let s2!: S | symbol;
+        `${s2}`;
+           ~~
+!!! error TS2731: Implicit conversion of a 'symbol' to a 'string' will fail at runtime. Consider wrapping this expression in 'String(...)'.
+        s2 + '';
+        ~~
+!!! error TS2469: The '+' operator cannot be applied to type 'symbol'.
+        +s2;
+         ~~
+!!! error TS2469: The '+' operator cannot be applied to type 'symbol'.
+    }
     
\ No newline at end of file
diff --git a/tests/baselines/reference/noImplicitSymbolToString.js b/tests/baselines/reference/noImplicitSymbolToString.js
index fed276b8a731e..68f581faa3924 100644
--- a/tests/baselines/reference/noImplicitSymbolToString.js
+++ b/tests/baselines/reference/noImplicitSymbolToString.js
@@ -12,6 +12,39 @@ let symbolUnionNumber!: symbol | number;
 let symbolUnionString!: symbol | string;
 
 const templateStrUnion = `union with number ${symbolUnionNumber} and union with string ${symbolUnionString}`;
+
+
+// Fix #44462
+
+type StringOrSymbol = string | symbol;
+
+function getKey<S extends StringOrSymbol>(key: S) {
+    return `${key} is the key`;
+}
+
+function getKey1<S extends symbol>(key: S) {
+    let s1!: S;
+    `${s1}`;
+    s1 + '';
+    +s1;
+
+    let s2!: S | string;
+    `${s2}`;
+    s2 + '';
+    +s2;
+}
+
+function getKey2<S extends string>(key: S) {
+    let s1!: S;
+    `${s1}`;
+    s1 + '';
+    +s1;
+
+    let s2!: S | symbol;
+    `${s2}`;
+    s2 + '';
+    +s2;
+}
 
 
 //// [noImplicitSymbolToString.js]
@@ -24,3 +57,26 @@ str += symbol;
 var symbolUnionNumber;
 var symbolUnionString;
 var templateStrUnion = "union with number ".concat(symbolUnionNumber, " and union with string ").concat(symbolUnionString);
+function getKey(key) {
+    return "".concat(key, " is the key");
+}
+function getKey1(key) {
+    var s1;
+    "".concat(s1);
+    s1 + '';
+    +s1;
+    var s2;
+    "".concat(s2);
+    s2 + '';
+    +s2;
+}
+function getKey2(key) {
+    var s1;
+    "".concat(s1);
+    s1 + '';
+    +s1;
+    var s2;
+    "".concat(s2);
+    s2 + '';
+    +s2;
+}
diff --git a/tests/baselines/reference/noImplicitSymbolToString.symbols b/tests/baselines/reference/noImplicitSymbolToString.symbols
index b2a08e151ab64..4922e1a112c99 100644
--- a/tests/baselines/reference/noImplicitSymbolToString.symbols
+++ b/tests/baselines/reference/noImplicitSymbolToString.symbols
@@ -30,3 +30,86 @@ const templateStrUnion = `union with number ${symbolUnionNumber} and union with
 >symbolUnionNumber : Symbol(symbolUnionNumber, Decl(noImplicitSymbolToString.ts, 9, 3))
 >symbolUnionString : Symbol(symbolUnionString, Decl(noImplicitSymbolToString.ts, 10, 3))
 
+
+// Fix #44462
+
+type StringOrSymbol = string | symbol;
+>StringOrSymbol : Symbol(StringOrSymbol, Decl(noImplicitSymbolToString.ts, 12, 109))
+
+function getKey<S extends StringOrSymbol>(key: S) {
+>getKey : Symbol(getKey, Decl(noImplicitSymbolToString.ts, 17, 38))
+>S : Symbol(S, Decl(noImplicitSymbolToString.ts, 19, 16))
+>StringOrSymbol : Symbol(StringOrSymbol, Decl(noImplicitSymbolToString.ts, 12, 109))
+>key : Symbol(key, Decl(noImplicitSymbolToString.ts, 19, 42))
+>S : Symbol(S, Decl(noImplicitSymbolToString.ts, 19, 16))
+
+    return `${key} is the key`;
+>key : Symbol(key, Decl(noImplicitSymbolToString.ts, 19, 42))
+}
+
+function getKey1<S extends symbol>(key: S) {
+>getKey1 : Symbol(getKey1, Decl(noImplicitSymbolToString.ts, 21, 1))
+>S : Symbol(S, Decl(noImplicitSymbolToString.ts, 23, 17))
+>key : Symbol(key, Decl(noImplicitSymbolToString.ts, 23, 35))
+>S : Symbol(S, Decl(noImplicitSymbolToString.ts, 23, 17))
+
+    let s1!: S;
+>s1 : Symbol(s1, Decl(noImplicitSymbolToString.ts, 24, 7))
+>S : Symbol(S, Decl(noImplicitSymbolToString.ts, 23, 17))
+
+    `${s1}`;
+>s1 : Symbol(s1, Decl(noImplicitSymbolToString.ts, 24, 7))
+
+    s1 + '';
+>s1 : Symbol(s1, Decl(noImplicitSymbolToString.ts, 24, 7))
+
+    +s1;
+>s1 : Symbol(s1, Decl(noImplicitSymbolToString.ts, 24, 7))
+
+    let s2!: S | string;
+>s2 : Symbol(s2, Decl(noImplicitSymbolToString.ts, 29, 7))
+>S : Symbol(S, Decl(noImplicitSymbolToString.ts, 23, 17))
+
+    `${s2}`;
+>s2 : Symbol(s2, Decl(noImplicitSymbolToString.ts, 29, 7))
+
+    s2 + '';
+>s2 : Symbol(s2, Decl(noImplicitSymbolToString.ts, 29, 7))
+
+    +s2;
+>s2 : Symbol(s2, Decl(noImplicitSymbolToString.ts, 29, 7))
+}
+
+function getKey2<S extends string>(key: S) {
+>getKey2 : Symbol(getKey2, Decl(noImplicitSymbolToString.ts, 33, 1))
+>S : Symbol(S, Decl(noImplicitSymbolToString.ts, 35, 17))
+>key : Symbol(key, Decl(noImplicitSymbolToString.ts, 35, 35))
+>S : Symbol(S, Decl(noImplicitSymbolToString.ts, 35, 17))
+
+    let s1!: S;
+>s1 : Symbol(s1, Decl(noImplicitSymbolToString.ts, 36, 7))
+>S : Symbol(S, Decl(noImplicitSymbolToString.ts, 35, 17))
+
+    `${s1}`;
+>s1 : Symbol(s1, Decl(noImplicitSymbolToString.ts, 36, 7))
+
+    s1 + '';
+>s1 : Symbol(s1, Decl(noImplicitSymbolToString.ts, 36, 7))
+
+    +s1;
+>s1 : Symbol(s1, Decl(noImplicitSymbolToString.ts, 36, 7))
+
+    let s2!: S | symbol;
+>s2 : Symbol(s2, Decl(noImplicitSymbolToString.ts, 41, 7))
+>S : Symbol(S, Decl(noImplicitSymbolToString.ts, 35, 17))
+
+    `${s2}`;
+>s2 : Symbol(s2, Decl(noImplicitSymbolToString.ts, 41, 7))
+
+    s2 + '';
+>s2 : Symbol(s2, Decl(noImplicitSymbolToString.ts, 41, 7))
+
+    +s2;
+>s2 : Symbol(s2, Decl(noImplicitSymbolToString.ts, 41, 7))
+}
+
diff --git a/tests/baselines/reference/noImplicitSymbolToString.types b/tests/baselines/reference/noImplicitSymbolToString.types
index c21c0e07bfded..7111542c4a318 100644
--- a/tests/baselines/reference/noImplicitSymbolToString.types
+++ b/tests/baselines/reference/noImplicitSymbolToString.types
@@ -36,3 +36,92 @@ const templateStrUnion = `union with number ${symbolUnionNumber} and union with
 >symbolUnionNumber : number | symbol
 >symbolUnionString : string | symbol
 
+
+// Fix #44462
+
+type StringOrSymbol = string | symbol;
+>StringOrSymbol : StringOrSymbol
+
+function getKey<S extends StringOrSymbol>(key: S) {
+>getKey : <S extends StringOrSymbol>(key: S) => string
+>key : S
+
+    return `${key} is the key`;
+>`${key} is the key` : string
+>key : S
+}
+
+function getKey1<S extends symbol>(key: S) {
+>getKey1 : <S extends symbol>(key: S) => void
+>key : S
+
+    let s1!: S;
+>s1 : S
+
+    `${s1}`;
+>`${s1}` : string
+>s1 : S
+
+    s1 + '';
+>s1 + '' : string
+>s1 : S
+>'' : ""
+
+    +s1;
+>+s1 : number
+>s1 : S
+
+    let s2!: S | string;
+>s2 : string | S
+
+    `${s2}`;
+>`${s2}` : string
+>s2 : string | S
+
+    s2 + '';
+>s2 + '' : string
+>s2 : string | S
+>'' : ""
+
+    +s2;
+>+s2 : number
+>s2 : string | S
+}
+
+function getKey2<S extends string>(key: S) {
+>getKey2 : <S extends string>(key: S) => void
+>key : S
+
+    let s1!: S;
+>s1 : S
+
+    `${s1}`;
+>`${s1}` : string
+>s1 : S
+
+    s1 + '';
+>s1 + '' : string
+>s1 : S
+>'' : ""
+
+    +s1;
+>+s1 : number
+>s1 : S
+
+    let s2!: S | symbol;
+>s2 : symbol | S
+
+    `${s2}`;
+>`${s2}` : string
+>s2 : symbol | S
+
+    s2 + '';
+>s2 + '' : string
+>s2 : symbol | S
+>'' : ""
+
+    +s2;
+>+s2 : number
+>s2 : symbol | S
+}
+
diff --git a/tests/cases/compiler/noImplicitSymbolToString.ts b/tests/cases/compiler/noImplicitSymbolToString.ts
index 16690d6d845cb..a3a797c5f67a8 100644
--- a/tests/cases/compiler/noImplicitSymbolToString.ts
+++ b/tests/cases/compiler/noImplicitSymbolToString.ts
@@ -11,3 +11,36 @@ let symbolUnionNumber!: symbol | number;
 let symbolUnionString!: symbol | string;
 
 const templateStrUnion = `union with number ${symbolUnionNumber} and union with string ${symbolUnionString}`;
+
+
+// Fix #44462
+
+type StringOrSymbol = string | symbol;
+
+function getKey<S extends StringOrSymbol>(key: S) {
+    return `${key} is the key`;
+}
+
+function getKey1<S extends symbol>(key: S) {
+    let s1!: S;
+    `${s1}`;
+    s1 + '';
+    +s1;
+
+    let s2!: S | string;
+    `${s2}`;
+    s2 + '';
+    +s2;
+}
+
+function getKey2<S extends string>(key: S) {
+    let s1!: S;
+    `${s1}`;
+    s1 + '';
+    +s1;
+
+    let s2!: S | symbol;
+    `${s2}`;
+    s2 + '';
+    +s2;
+}