diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index a4020504f9c07..253561ae81b66 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -23832,7 +23832,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             findMostOverlappyType(source, target);
     }
 
-    function discriminateTypeByDiscriminableItems(target: UnionType, discriminators: (readonly [() => Type, __String])[], related: (source: Type, target: Type) => boolean | Ternary) {
+    function discriminateTypeByDiscriminableItems(target: UnionType, discriminators: (readonly [() => Type, __String | number])[], related: (source: Type, target: Type) => boolean | Ternary) {
         const types = target.types;
         const include: Ternary[] = types.map(t => t.flags & TypeFlags.Primitive ? Ternary.False : Ternary.True);
         for (const [getDiscriminatingType, propertyName] of discriminators) {
@@ -23842,7 +23842,9 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             let matched = false;
             for (let i = 0; i < types.length; i++) {
                 if (include[i]) {
-                    const targetType = getTypeOfPropertyOrIndexSignatureOfType(types[i], propertyName);
+                    const targetType = typeof propertyName === "number"
+                        ? getContextualTypeForElementExpression(types[i], propertyName)
+                        : getTypeOfPropertyOrIndexSignatureOfType(types[i], propertyName);
                     if (targetType && related(getDiscriminatingType(), targetType)) {
                         matched = true;
                     }
@@ -31361,6 +31363,25 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         );
     }
 
+    function discriminateContextualTypeByElements(node: ArrayLiteralExpression, contextualType: UnionType) {
+        const key = `D${getNodeId(node)},${getTypeId(contextualType)}`;
+        const cached = getCachedType(key);
+        if (cached) return cached;
+
+        // Create a discriminator for each element in the list
+        const discriminators = map(
+            node.elements,
+            (e, ndx) => [() => getContextFreeTypeOfExpression(e), ndx] as const,
+        );
+        const discriminatedType = discriminateTypeByDiscriminableItems(
+            contextualType,
+            discriminators,
+            isTypeAssignableTo,
+        );
+
+        return setCachedType(key, discriminatedType);
+    }
+
     // Return the contextual type for a given expression node. During overload resolution, a contextual type may temporarily
     // be "pushed" onto a node using the contextualType property.
     function getApparentTypeOfContextualType(node: Expression | MethodDeclaration, contextFlags: ContextFlags | undefined): Type | undefined {
@@ -31378,9 +31399,19 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 t => getObjectFlags(t) & ObjectFlags.Mapped ? t : getApparentType(t),
                 /*noReductions*/ true,
             );
-            return apparentType.flags & TypeFlags.Union && isObjectLiteralExpression(node) ? discriminateContextualTypeByObjectMembers(node, apparentType as UnionType) :
-                apparentType.flags & TypeFlags.Union && isJsxAttributes(node) ? discriminateContextualTypeByJSXAttributes(node, apparentType as UnionType) :
-                apparentType;
+            const isUnion = apparentType.flags & TypeFlags.Union;
+            if (isUnion && isObjectLiteralExpression(node)) {
+                return discriminateContextualTypeByObjectMembers(node, apparentType as UnionType);
+            }
+            else if (isUnion && isJsxAttributes(node)) {
+                return discriminateContextualTypeByJSXAttributes(node, apparentType as UnionType);
+            }
+            else if (contextFlags && contextFlags & ContextFlags.Completions && isUnion && isArrayLiteralExpression(node)) {
+                return discriminateContextualTypeByElements(node, instantiatedType as UnionType);
+            }
+            else {
+                return apparentType;
+            }
         }
     }
 
diff --git a/src/services/stringCompletions.ts b/src/services/stringCompletions.ts
index 06f488ed47bcb..39516382d1d62 100644
--- a/src/services/stringCompletions.ts
+++ b/src/services/stringCompletions.ts
@@ -479,7 +479,8 @@ function getStringLiteralCompletionEntries(sourceFile: SourceFile, node: StringL
     function fromContextualType(contextFlags: ContextFlags = ContextFlags.Completions): StringLiteralCompletionsFromTypes | undefined {
         // Get completion for string literal from string literal type
         // i.e. var x: "hi" | "hello" = "/*completion position*/"
-        const types = getStringLiteralTypes(getContextualTypeFromParent(node, typeChecker, contextFlags));
+        const contextualType = getContextualTypeFromParent(node, typeChecker, contextFlags);
+        const types = getStringLiteralTypes(contextualType);
         if (!types.length) {
             return;
         }
@@ -552,8 +553,12 @@ function stringLiteralCompletionsForObjectLiteral(checker: TypeChecker, objectLi
 function getStringLiteralTypes(type: Type | undefined, uniques = new Map<string, true>()): readonly StringLiteralType[] {
     if (!type) return emptyArray;
     type = skipConstraint(type);
-    return type.isUnion() ? flatMap(type.types, t => getStringLiteralTypes(t, uniques)) :
-        type.isStringLiteral() && !(type.flags & TypeFlags.EnumLiteral) && addToSeen(uniques, type.value) ? [type] : emptyArray;
+    if (type.isUnion()) {
+        return flatMap(type.types, t => getStringLiteralTypes(t, uniques));
+    }
+    else {
+        return type.isStringLiteral() && !(type.flags & TypeFlags.EnumLiteral) && addToSeen(uniques, type.value) ? [type] : emptyArray;
+    }
 }
 
 interface NameAndKind {
diff --git a/tests/cases/fourslash/completionsTuple.ts b/tests/cases/fourslash/completionsTuple1.ts
similarity index 100%
rename from tests/cases/fourslash/completionsTuple.ts
rename to tests/cases/fourslash/completionsTuple1.ts
diff --git a/tests/cases/fourslash/completionsTuple2.ts b/tests/cases/fourslash/completionsTuple2.ts
new file mode 100644
index 0000000000000..45448a2c799fe
--- /dev/null
+++ b/tests/cases/fourslash/completionsTuple2.ts
@@ -0,0 +1,5 @@
+/// <reference path="fourslash.ts" />
+
+////declare const x: ["a", "b"]  = ["x", "/**/"]
+
+verify.completions({ marker: "", exact: ["b"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTuple3.ts b/tests/cases/fourslash/completionsTuple3.ts
new file mode 100644
index 0000000000000..73ae138ef310c
--- /dev/null
+++ b/tests/cases/fourslash/completionsTuple3.ts
@@ -0,0 +1,5 @@
+/// <reference path="fourslash.ts" />
+
+////declare const x: ["a", ["b"], "x", ["y"]] = ["a", ["/**/"]]
+
+verify.completions({ marker: "", exact: ["b"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion1.ts b/tests/cases/fourslash/completionsTupleUnion1.ts
new file mode 100644
index 0000000000000..9d2fc2d536b86
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion1.ts
@@ -0,0 +1,6 @@
+/// <reference path="fourslash.ts" />
+
+////declare const a: "a";
+////declare const x: ['a', 'b'] | ['a', 'c'] | ['d', 'e'] = [a, "/**/"];
+
+verify.completions({ marker: "", exact: ["b", "c"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion10.ts b/tests/cases/fourslash/completionsTupleUnion10.ts
new file mode 100644
index 0000000000000..a882034881d93
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion10.ts
@@ -0,0 +1,4 @@
+/// <reference path="fourslash.ts" />
+////declare const x: ['a', 'b'] | { '0': 'x', '1': 'y' } | { '1': 'z' } = ['x', '/**/'];
+
+verify.completions({ marker: "", exact: ["y"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion11.ts b/tests/cases/fourslash/completionsTupleUnion11.ts
new file mode 100644
index 0000000000000..4061546914057
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion11.ts
@@ -0,0 +1,5 @@
+/// <reference path="fourslash.ts" />
+////type ABC = "a" | "b" | "c";
+////declare const x: ['abc', ...ABC[]] | ['abc', 'abc', "f"] = ['abc', 'abc', '/**/'];
+
+verify.completions({ marker: "", exact: ["f"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion12.ts b/tests/cases/fourslash/completionsTupleUnion12.ts
new file mode 100644
index 0000000000000..46228aadf7bfa
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion12.ts
@@ -0,0 +1,4 @@
+/// <reference path="fourslash.ts" />
+////declare const x: [(arg: number) => void, "num"] | [(arg: string) => void, "str"] | [(arg: boolean) => boolean, "val"] = [() => {}, '/**/'];
+
+verify.completions({ marker: "", exact: ["num", "str"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion13.ts b/tests/cases/fourslash/completionsTupleUnion13.ts
new file mode 100644
index 0000000000000..93f35e9e93af6
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion13.ts
@@ -0,0 +1,4 @@
+/// <reference path="fourslash.ts" />
+////declare const x: [(arg: number) => void, "num"] | [(arg: string) => void, "str"] | [(arg: number) => number, "num2"] = [(x: number) => {}, '/**/'];
+
+verify.completions({ marker: "", exact: ["num"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion2.ts b/tests/cases/fourslash/completionsTupleUnion2.ts
new file mode 100644
index 0000000000000..7ca2cf7b55646
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion2.ts
@@ -0,0 +1,6 @@
+/// <reference path="fourslash.ts" />
+
+////declare const a: "a";
+////declare const x: [{ t: "a" }, "b"] | [{ t: "b" }, "c"]  = [{ t: a }, "/**/"]
+
+verify.completions({ marker: "", exact: ["b"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion3.ts b/tests/cases/fourslash/completionsTupleUnion3.ts
new file mode 100644
index 0000000000000..33aea75271793
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion3.ts
@@ -0,0 +1,6 @@
+/// <reference path="fourslash.ts" />
+
+////declare const a: "a";
+////declare const x: ['a', 'b', 'f'] | ['a', 'b'] = [a, 'b', "/**/"];
+
+verify.completions({ marker: "", exact: ["f"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion4.ts b/tests/cases/fourslash/completionsTupleUnion4.ts
new file mode 100644
index 0000000000000..ad4b3e0db6b13
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion4.ts
@@ -0,0 +1,5 @@
+/// <reference path="fourslash.ts" />
+
+////declare const x: ['a', 'b', 'f', 'g'] | ['a', 'b'] = ["a", 'b', 'f', "/**/"];
+
+verify.completions({ marker: "", exact: ["g"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion5.ts b/tests/cases/fourslash/completionsTupleUnion5.ts
new file mode 100644
index 0000000000000..ad1108b2c81f8
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion5.ts
@@ -0,0 +1,5 @@
+/// <reference path="fourslash.ts" />
+
+////declare const x: ['a', 'b'] | ['a', 'c'] = ['b', "/**/"];
+
+verify.completions({ marker: "", exact: ["b", "c"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion6.ts b/tests/cases/fourslash/completionsTupleUnion6.ts
new file mode 100644
index 0000000000000..1e7a5bd824aba
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion6.ts
@@ -0,0 +1,5 @@
+/// <reference path="fourslash.ts" />
+
+////declare const x: ['a', 'v1'] | ['b', 'v2'] = ['b', "v/**/"];
+
+verify.completions({ marker: "", exact: ["v2"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion7.ts b/tests/cases/fourslash/completionsTupleUnion7.ts
new file mode 100644
index 0000000000000..af426152f99d1
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion7.ts
@@ -0,0 +1,6 @@
+/// <reference path="fourslash.ts" />
+////type ABC = "a" | "b" | "c";
+////type XYZ = "x" | "y" | "z";
+////declare const x: ['abc', ABC] | ['xyz', ...XYZ[]] = ['xyz', 'x', 'x', 'x', 'x', '/**/'];
+
+verify.completions({ marker: "", exact: ["x", "y", "z"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion8.ts b/tests/cases/fourslash/completionsTupleUnion8.ts
new file mode 100644
index 0000000000000..03039dc86ca20
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion8.ts
@@ -0,0 +1,6 @@
+/// <reference path="fourslash.ts" />
+////type ABC = "a" | "b" | "c";
+////type XYZ = "x" | "y" | "z";
+////declare const x: ['abc', ...ABC[]] | ['xyz', ...XYZ[]] = ['abc', 'a', 'b', 'c', 'a', '/**/'];
+
+verify.completions({ marker: "", exact: ["a", "b", "c"] });
\ No newline at end of file
diff --git a/tests/cases/fourslash/completionsTupleUnion9.ts b/tests/cases/fourslash/completionsTupleUnion9.ts
new file mode 100644
index 0000000000000..3951f3b4e7cc6
--- /dev/null
+++ b/tests/cases/fourslash/completionsTupleUnion9.ts
@@ -0,0 +1,5 @@
+/// <reference path="fourslash.ts" />
+////type ABC = "a" | "b" | "c";
+////declare const x: ['abc', ...ABC[]] | ['abc', "a", "f"] = ['abc', 'a', '/**/'];
+
+verify.completions({ marker: "", exact: ["a", "b", "c", "f"] });
\ No newline at end of file