diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index afd1251f4a..b3a63ac74e 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -14457,11 +14457,20 @@ namespace ts {
                 return elaborateElementwise(generateLimitedTupleElements(node, target), source, target, relation, containingMessageChain, errorOutputContainer);
             }
             // recreate a tuple from the elements, if possible
-            const tupleizedType = checkArrayLiteral(node, CheckMode.Contextual, /*forceTuple*/ true);
-            if (isTupleLikeType(tupleizedType)) {
-                return elaborateElementwise(generateLimitedTupleElements(node, target), tupleizedType, target, relation, containingMessageChain, errorOutputContainer);
+            // Since we're re-doing the expression type, we need to reapply the contextual type
+            const oldContext = node.contextualType;
+            node.contextualType = target;
+            try {
+                const tupleizedType = checkArrayLiteral(node, CheckMode.Contextual, /*forceTuple*/ true);
+                node.contextualType = oldContext;
+                if (isTupleLikeType(tupleizedType)) {
+                    return elaborateElementwise(generateLimitedTupleElements(node, target), tupleizedType, target, relation, containingMessageChain, errorOutputContainer);
+                }
+                return false;
+            }
+            finally {
+                node.contextualType = oldContext;
             }
-            return false;
         }
 
         function *generateObjectLiteralElements(node: ObjectLiteralExpression): ElaborationIterator {
diff --git a/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.errors.txt b/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.errors.txt
new file mode 100644
index 0000000000..93996556e6
--- /dev/null
+++ b/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.errors.txt
@@ -0,0 +1,29 @@
+tests/cases/compiler/errorsForCallAndAssignmentAreSimilar.ts(11,11): error TS2322: Type '"hdpvd"' is not assignable to type '"hddvd" | "bluray"'.
+tests/cases/compiler/errorsForCallAndAssignmentAreSimilar.ts(16,11): error TS2322: Type '"hdpvd"' is not assignable to type '"hddvd" | "bluray"'.
+
+
+==== tests/cases/compiler/errorsForCallAndAssignmentAreSimilar.ts (2 errors) ====
+    function minimalExample1() {
+        type Disc =
+            | { kind: "hddvd" }
+            | { kind: "bluray" }
+    
+        function foo(x: Disc[]) {
+        }
+    
+        foo([
+            { kind: "bluray", },
+            { kind: "hdpvd", }
+              ~~~~
+!!! error TS2322: Type '"hdpvd"' is not assignable to type '"hddvd" | "bluray"'.
+!!! related TS6500 tests/cases/compiler/errorsForCallAndAssignmentAreSimilar.ts:3:13: The expected type comes from property 'kind' which is declared here on type 'Disc'
+        ]);
+    
+        const ds: Disc[] = [
+            { kind: "bluray", },
+            { kind: "hdpvd", }
+              ~~~~
+!!! error TS2322: Type '"hdpvd"' is not assignable to type '"hddvd" | "bluray"'.
+!!! related TS6500 tests/cases/compiler/errorsForCallAndAssignmentAreSimilar.ts:3:13: The expected type comes from property 'kind' which is declared here on type 'Disc'
+        ];
+    }
\ No newline at end of file
diff --git a/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.js b/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.js
new file mode 100644
index 0000000000..72a043f0d8
--- /dev/null
+++ b/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.js
@@ -0,0 +1,33 @@
+//// [errorsForCallAndAssignmentAreSimilar.ts]
+function minimalExample1() {
+    type Disc =
+        | { kind: "hddvd" }
+        | { kind: "bluray" }
+
+    function foo(x: Disc[]) {
+    }
+
+    foo([
+        { kind: "bluray", },
+        { kind: "hdpvd", }
+    ]);
+
+    const ds: Disc[] = [
+        { kind: "bluray", },
+        { kind: "hdpvd", }
+    ];
+}
+
+//// [errorsForCallAndAssignmentAreSimilar.js]
+function minimalExample1() {
+    function foo(x) {
+    }
+    foo([
+        { kind: "bluray" },
+        { kind: "hdpvd" }
+    ]);
+    var ds = [
+        { kind: "bluray" },
+        { kind: "hdpvd" }
+    ];
+}
diff --git a/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.symbols b/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.symbols
new file mode 100644
index 0000000000..e29e884697
--- /dev/null
+++ b/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.symbols
@@ -0,0 +1,42 @@
+=== tests/cases/compiler/errorsForCallAndAssignmentAreSimilar.ts ===
+function minimalExample1() {
+>minimalExample1 : Symbol(minimalExample1, Decl(errorsForCallAndAssignmentAreSimilar.ts, 0, 0))
+
+    type Disc =
+>Disc : Symbol(Disc, Decl(errorsForCallAndAssignmentAreSimilar.ts, 0, 28))
+
+        | { kind: "hddvd" }
+>kind : Symbol(kind, Decl(errorsForCallAndAssignmentAreSimilar.ts, 2, 11))
+
+        | { kind: "bluray" }
+>kind : Symbol(kind, Decl(errorsForCallAndAssignmentAreSimilar.ts, 3, 11))
+
+    function foo(x: Disc[]) {
+>foo : Symbol(foo, Decl(errorsForCallAndAssignmentAreSimilar.ts, 3, 28))
+>x : Symbol(x, Decl(errorsForCallAndAssignmentAreSimilar.ts, 5, 17))
+>Disc : Symbol(Disc, Decl(errorsForCallAndAssignmentAreSimilar.ts, 0, 28))
+    }
+
+    foo([
+>foo : Symbol(foo, Decl(errorsForCallAndAssignmentAreSimilar.ts, 3, 28))
+
+        { kind: "bluray", },
+>kind : Symbol(kind, Decl(errorsForCallAndAssignmentAreSimilar.ts, 9, 9))
+
+        { kind: "hdpvd", }
+>kind : Symbol(kind, Decl(errorsForCallAndAssignmentAreSimilar.ts, 10, 9))
+
+    ]);
+
+    const ds: Disc[] = [
+>ds : Symbol(ds, Decl(errorsForCallAndAssignmentAreSimilar.ts, 13, 9))
+>Disc : Symbol(Disc, Decl(errorsForCallAndAssignmentAreSimilar.ts, 0, 28))
+
+        { kind: "bluray", },
+>kind : Symbol(kind, Decl(errorsForCallAndAssignmentAreSimilar.ts, 14, 9))
+
+        { kind: "hdpvd", }
+>kind : Symbol(kind, Decl(errorsForCallAndAssignmentAreSimilar.ts, 15, 9))
+
+    ];
+}
diff --git a/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.types b/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.types
new file mode 100644
index 0000000000..6f22f7f499
--- /dev/null
+++ b/tests/baselines/reference/errorsForCallAndAssignmentAreSimilar.types
@@ -0,0 +1,51 @@
+=== tests/cases/compiler/errorsForCallAndAssignmentAreSimilar.ts ===
+function minimalExample1() {
+>minimalExample1 : () => void
+
+    type Disc =
+>Disc : { kind: "hddvd"; } | { kind: "bluray"; }
+
+        | { kind: "hddvd" }
+>kind : "hddvd"
+
+        | { kind: "bluray" }
+>kind : "bluray"
+
+    function foo(x: Disc[]) {
+>foo : (x: ({ kind: "hddvd"; } | { kind: "bluray"; })[]) => void
+>x : ({ kind: "hddvd"; } | { kind: "bluray"; })[]
+    }
+
+    foo([
+>foo([        { kind: "bluray", },        { kind: "hdpvd", }    ]) : void
+>foo : (x: ({ kind: "hddvd"; } | { kind: "bluray"; })[]) => void
+>[        { kind: "bluray", },        { kind: "hdpvd", }    ] : ({ kind: "bluray"; } | { kind: "hdpvd"; })[]
+
+        { kind: "bluray", },
+>{ kind: "bluray", } : { kind: "bluray"; }
+>kind : "bluray"
+>"bluray" : "bluray"
+
+        { kind: "hdpvd", }
+>{ kind: "hdpvd", } : { kind: "hdpvd"; }
+>kind : "hdpvd"
+>"hdpvd" : "hdpvd"
+
+    ]);
+
+    const ds: Disc[] = [
+>ds : ({ kind: "hddvd"; } | { kind: "bluray"; })[]
+>[        { kind: "bluray", },        { kind: "hdpvd", }    ] : ({ kind: "bluray"; } | { kind: "hdpvd"; })[]
+
+        { kind: "bluray", },
+>{ kind: "bluray", } : { kind: "bluray"; }
+>kind : "bluray"
+>"bluray" : "bluray"
+
+        { kind: "hdpvd", }
+>{ kind: "hdpvd", } : { kind: "hdpvd"; }
+>kind : "hdpvd"
+>"hdpvd" : "hdpvd"
+
+    ];
+}
diff --git a/tests/cases/compiler/errorsForCallAndAssignmentAreSimilar.ts b/tests/cases/compiler/errorsForCallAndAssignmentAreSimilar.ts
new file mode 100644
index 0000000000..218397dfb7
--- /dev/null
+++ b/tests/cases/compiler/errorsForCallAndAssignmentAreSimilar.ts
@@ -0,0 +1,18 @@
+function minimalExample1() {
+    type Disc =
+        | { kind: "hddvd" }
+        | { kind: "bluray" }
+
+    function foo(x: Disc[]) {
+    }
+
+    foo([
+        { kind: "bluray", },
+        { kind: "hdpvd", }
+    ]);
+
+    const ds: Disc[] = [
+        { kind: "bluray", },
+        { kind: "hdpvd", }
+    ];
+}
\ No newline at end of file