diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 26b93b19335b4..0b357bd771da4 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -13900,6 +13900,18 @@ namespace ts {
             return flow.id;
         }
 
+        function typeMaybeAssignableTo(source: Type, target: Type) {
+            if (!(source.flags & TypeFlags.Union)) {
+                return isTypeAssignableTo(source, target);
+            }
+            for (const t of (<UnionType>source).types) {
+                if (isTypeAssignableTo(t, target)) {
+                    return true;
+                }
+            }
+            return false;
+        }
+
         // Remove those constituent types of declaredType to which no constituent type of assignedType is assignable.
         // For example, when a variable of type number | string | boolean is assigned a value of type number | boolean,
         // we remove type string.
@@ -13908,8 +13920,12 @@ namespace ts {
                 if (assignedType.flags & TypeFlags.Never) {
                     return assignedType;
                 }
-                const reducedType = filterType(declaredType, t => isTypeComparableTo(assignedType, t));
-                if (!(reducedType.flags & TypeFlags.Never)) {
+                const reducedType = filterType(declaredType, t => typeMaybeAssignableTo(assignedType, t));
+                // Our crude heuristic produces an invalid result in some cases: see GH#26130.
+                // For now, when that happens, we give up and don't narrow at all.  (This also
+                // means we'll never narrow for erroneous assignments where the assigned type
+                // is not assignable to the declared type.)
+                if (isTypeAssignableTo(assignedType, reducedType)) {
                     return reducedType;
                 }
             }
diff --git a/tests/baselines/reference/assignmentTypeNarrowing.js b/tests/baselines/reference/assignmentTypeNarrowing.js
index 4d6b911b88b93..24a08539eb7d2 100644
--- a/tests/baselines/reference/assignmentTypeNarrowing.js
+++ b/tests/baselines/reference/assignmentTypeNarrowing.js
@@ -27,6 +27,12 @@ let a: string[];
 for (x of a) {
     x; // string
 }
+
+// Repro from #26405
+
+type AOrArrA<T> = T | T[];
+const arr: AOrArrA<{x?: "ok"}> = [{ x: "ok" }]; // weak type
+arr.push({ x: "ok" });
 
 
 //// [assignmentTypeNarrowing.js]
@@ -51,3 +57,5 @@ for (var _i = 0, a_1 = a; _i < a_1.length; _i++) {
     x = a_1[_i];
     x; // string
 }
+var arr = [{ x: "ok" }]; // weak type
+arr.push({ x: "ok" });
diff --git a/tests/baselines/reference/assignmentTypeNarrowing.symbols b/tests/baselines/reference/assignmentTypeNarrowing.symbols
index b9e8f3f136d21..36a2cf44dae8e 100644
--- a/tests/baselines/reference/assignmentTypeNarrowing.symbols
+++ b/tests/baselines/reference/assignmentTypeNarrowing.symbols
@@ -62,3 +62,23 @@ for (x of a) {
 >x : Symbol(x, Decl(assignmentTypeNarrowing.ts, 0, 3))
 }
 
+// Repro from #26405
+
+type AOrArrA<T> = T | T[];
+>AOrArrA : Symbol(AOrArrA, Decl(assignmentTypeNarrowing.ts, 27, 1))
+>T : Symbol(T, Decl(assignmentTypeNarrowing.ts, 31, 13))
+>T : Symbol(T, Decl(assignmentTypeNarrowing.ts, 31, 13))
+>T : Symbol(T, Decl(assignmentTypeNarrowing.ts, 31, 13))
+
+const arr: AOrArrA<{x?: "ok"}> = [{ x: "ok" }]; // weak type
+>arr : Symbol(arr, Decl(assignmentTypeNarrowing.ts, 32, 5))
+>AOrArrA : Symbol(AOrArrA, Decl(assignmentTypeNarrowing.ts, 27, 1))
+>x : Symbol(x, Decl(assignmentTypeNarrowing.ts, 32, 20))
+>x : Symbol(x, Decl(assignmentTypeNarrowing.ts, 32, 35))
+
+arr.push({ x: "ok" });
+>arr.push : Symbol(Array.push, Decl(lib.es5.d.ts, --, --))
+>arr : Symbol(arr, Decl(assignmentTypeNarrowing.ts, 32, 5))
+>push : Symbol(Array.push, Decl(lib.es5.d.ts, --, --))
+>x : Symbol(x, Decl(assignmentTypeNarrowing.ts, 33, 10))
+
diff --git a/tests/baselines/reference/assignmentTypeNarrowing.types b/tests/baselines/reference/assignmentTypeNarrowing.types
index 2e2e6ad44eb04..15b71c259aef8 100644
--- a/tests/baselines/reference/assignmentTypeNarrowing.types
+++ b/tests/baselines/reference/assignmentTypeNarrowing.types
@@ -96,3 +96,25 @@ for (x of a) {
 >x : string
 }
 
+// Repro from #26405
+
+type AOrArrA<T> = T | T[];
+>AOrArrA : AOrArrA<T>
+
+const arr: AOrArrA<{x?: "ok"}> = [{ x: "ok" }]; // weak type
+>arr : AOrArrA<{ x?: "ok"; }>
+>x : "ok"
+>[{ x: "ok" }] : { x: "ok"; }[]
+>{ x: "ok" } : { x: "ok"; }
+>x : "ok"
+>"ok" : "ok"
+
+arr.push({ x: "ok" });
+>arr.push({ x: "ok" }) : number
+>arr.push : (...items: { x?: "ok"; }[]) => number
+>arr : { x?: "ok"; }[]
+>push : (...items: { x?: "ok"; }[]) => number
+>{ x: "ok" } : { x: "ok"; }
+>x : "ok"
+>"ok" : "ok"
+
diff --git a/tests/baselines/reference/enumAssignmentCompat3.types b/tests/baselines/reference/enumAssignmentCompat3.types
index f2a693515e581..a152cd624dfc1 100644
--- a/tests/baselines/reference/enumAssignmentCompat3.types
+++ b/tests/baselines/reference/enumAssignmentCompat3.types
@@ -252,9 +252,9 @@ abc = merged; // missing 'd'
 >merged : Merged.E
 
 merged = abc; // ok
->merged = abc : First.E.a | First.E.b
+>merged = abc : First.E
 >merged : Merged.E
->abc : First.E.a | First.E.b
+>abc : First.E
 
 abc = merged2; // ok
 >abc = merged2 : Merged2.E
diff --git a/tests/baselines/reference/numericLiteralTypes3.types b/tests/baselines/reference/numericLiteralTypes3.types
index 3fede24475c6a..9748eaccfcad5 100644
--- a/tests/baselines/reference/numericLiteralTypes3.types
+++ b/tests/baselines/reference/numericLiteralTypes3.types
@@ -118,9 +118,9 @@ function f4(a: A, b: B, c: C, d: D) {
 >c : C
 
     d = d;
->d = d : 1 | 2
+>d = d : D
+>d : D
 >d : D
->d : 1 | 2
 }
 
 function f5(a: A, b: B, c: C, d: D) {
diff --git a/tests/cases/conformance/expressions/assignmentOperator/assignmentTypeNarrowing.ts b/tests/cases/conformance/expressions/assignmentOperator/assignmentTypeNarrowing.ts
index 0e5e257635a57..19d12a1b81ae0 100644
--- a/tests/cases/conformance/expressions/assignmentOperator/assignmentTypeNarrowing.ts
+++ b/tests/cases/conformance/expressions/assignmentOperator/assignmentTypeNarrowing.ts
@@ -26,3 +26,9 @@ let a: string[];
 for (x of a) {
     x; // string
 }
+
+// Repro from #26405
+
+type AOrArrA<T> = T | T[];
+const arr: AOrArrA<{x?: "ok"}> = [{ x: "ok" }]; // weak type
+arr.push({ x: "ok" });