diff --git a/internal/checker/inference.go b/internal/checker/inference.go
index fb5da8b8226..b97d0e9e09e 100644
--- a/internal/checker/inference.go
+++ b/internal/checker/inference.go
@@ -108,10 +108,15 @@ func (c *Checker) inferFromTypes(n *InferenceState, source *Type, target *Type)
 		// First, infer between identically matching source and target constituents and remove the
 		// matching types.
 		tempSources, tempTargets := c.inferFromMatchingTypes(n, sourceTypes, target.Distributed(), (*Checker).isTypeOrBaseIdenticalTo)
+		// Next, infer between deeply matching source and target constituents and remove the
+		// matching types. Types deeply match when they are instantiations of the same object
+		// type and their type arguments have matching nesting structure. This prevents incorrect
+		// cross-matching of types like Array<T> with Array<T[]> in unions like T[] | T[][].
+		tempSources2, tempTargets2 := c.inferFromMatchingTypes(n, tempSources, tempTargets, (*Checker).isTypeDeeplyMatchedBy)
 		// Next, infer between closely matching source and target constituents and remove
 		// the matching types. Types closely match when they are instantiations of the same
 		// object type or instantiations of the same type alias.
-		sources, targets := c.inferFromMatchingTypes(n, tempSources, tempTargets, (*Checker).isTypeCloselyMatchedBy)
+		sources, targets := c.inferFromMatchingTypes(n, tempSources2, tempTargets2, (*Checker).isTypeCloselyMatchedBy)
 		if len(targets) == 0 {
 			return
 		}
@@ -1168,6 +1173,36 @@ func (c *Checker) isTypeCloselyMatchedBy(s *Type, t *Type) bool {
 		s.alias != nil && t.alias != nil && len(s.alias.typeArguments) != 0 && s.alias.symbol == t.alias.symbol
 }
 
+// isTypeDeeplyMatchedBy checks that two types are closely matched AND that their type arguments
+// have compatible nesting depth. This provides a more precise matching than isTypeCloselyMatchedBy
+// for cases like T[] | T[][] where all constituents share the same symbol (Array) but differ in
+// nesting depth, preventing cross-matching of Array<Value> with Array<Array<T>>.
+func (c *Checker) isTypeDeeplyMatchedBy(s *Type, t *Type) bool {
+	if !c.isTypeCloselyMatchedBy(s, t) {
+		return false
+	}
+	if s.objectFlags&ObjectFlagsReference != 0 && t.objectFlags&ObjectFlagsReference != 0 {
+		sr := s.AsTypeReference()
+		tr := t.AsTypeReference()
+		sArgs := c.getTypeArguments(s)
+		tArgs := c.getTypeArguments(t)
+		if len(sArgs) != len(tArgs) {
+			return false
+		}
+		for i := range sArgs {
+			// Check that type arguments have matching nesting structure: if the source arg
+			// is a nested reference to the same outer type (e.g., Array<Array<...>>), the
+			// target arg must also be nested, and vice versa.
+			saIsNestedRef := sArgs[i].objectFlags&ObjectFlagsReference != 0 && sArgs[i].AsTypeReference().target == sr.target
+			taIsNestedRef := tArgs[i].objectFlags&ObjectFlagsReference != 0 && tArgs[i].AsTypeReference().target == tr.target
+			if saIsNestedRef != taIsNestedRef {
+				return false
+			}
+		}
+	}
+	return true
+}
+
 // Create an object with properties named in the string literal type. Every property has type `any`.
 func (c *Checker) createEmptyObjectTypeFromStringLiteral(t *Type) *Type {
 	members := make(ast.SymbolTable)
diff --git a/testdata/baselines/reference/compiler/inferenceUnionArrayDepth.js b/testdata/baselines/reference/compiler/inferenceUnionArrayDepth.js
new file mode 100644
index 00000000000..270c46fe3e8
--- /dev/null
+++ b/testdata/baselines/reference/compiler/inferenceUnionArrayDepth.js
@@ -0,0 +1,52 @@
+//// [tests/cases/compiler/inferenceUnionArrayDepth.ts] ////
+
+//// [inferenceUnionArrayDepth.ts]
+// Regression test for https://github.com/microsoft/typescript-go/issues/1789
+// and https://github.com/microsoft/typescript-go/issues/3370
+// Inference should correctly infer T from T[] | T[][] union parameters.
+
+declare function flat<T>(args: T[] | T[][]): T;
+
+// Case 1: Union type (issue #1789)
+type Value = 1 | 2;
+declare const n: Value[] | Value[][];
+const result1: Value = flat(n); // Should infer T = Value, not T = Value[]
+
+// Case 2: Object type (issue #3370)
+type TG = { a: string };
+
+function isNestedArray<T>(arr: T[] | T[][]): arr is T[][] {
+    return Array.isArray(arr) && Array.isArray(arr[0]);
+}
+
+function convert(controls: TG[] | TG[][]): TG[][] {
+    if (isNestedArray(controls)) {
+        return controls;
+    } else {
+        return [controls];
+    }
+}
+
+// Case 3: Primitive type (should already work)
+declare const s: string[] | string[][];
+const result3: string = flat(s);
+
+
+//// [inferenceUnionArrayDepth.js]
+"use strict";
+// Regression test for https://github.com/microsoft/typescript-go/issues/1789
+// and https://github.com/microsoft/typescript-go/issues/3370
+// Inference should correctly infer T from T[] | T[][] union parameters.
+const result1 = flat(n); // Should infer T = Value, not T = Value[]
+function isNestedArray(arr) {
+    return Array.isArray(arr) && Array.isArray(arr[0]);
+}
+function convert(controls) {
+    if (isNestedArray(controls)) {
+        return controls;
+    }
+    else {
+        return [controls];
+    }
+}
+const result3 = flat(s);
diff --git a/testdata/baselines/reference/compiler/inferenceUnionArrayDepth.symbols b/testdata/baselines/reference/compiler/inferenceUnionArrayDepth.symbols
new file mode 100644
index 00000000000..e69e5061230
--- /dev/null
+++ b/testdata/baselines/reference/compiler/inferenceUnionArrayDepth.symbols
@@ -0,0 +1,84 @@
+//// [tests/cases/compiler/inferenceUnionArrayDepth.ts] ////
+
+=== inferenceUnionArrayDepth.ts ===
+// Regression test for https://github.com/microsoft/typescript-go/issues/1789
+// and https://github.com/microsoft/typescript-go/issues/3370
+// Inference should correctly infer T from T[] | T[][] union parameters.
+
+declare function flat<T>(args: T[] | T[][]): T;
+>flat : Symbol(flat, Decl(inferenceUnionArrayDepth.ts, 0, 0))
+>T : Symbol(T, Decl(inferenceUnionArrayDepth.ts, 4, 22))
+>args : Symbol(args, Decl(inferenceUnionArrayDepth.ts, 4, 25))
+>T : Symbol(T, Decl(inferenceUnionArrayDepth.ts, 4, 22))
+>T : Symbol(T, Decl(inferenceUnionArrayDepth.ts, 4, 22))
+>T : Symbol(T, Decl(inferenceUnionArrayDepth.ts, 4, 22))
+
+// Case 1: Union type (issue #1789)
+type Value = 1 | 2;
+>Value : Symbol(Value, Decl(inferenceUnionArrayDepth.ts, 4, 47))
+
+declare const n: Value[] | Value[][];
+>n : Symbol(n, Decl(inferenceUnionArrayDepth.ts, 8, 13))
+>Value : Symbol(Value, Decl(inferenceUnionArrayDepth.ts, 4, 47))
+>Value : Symbol(Value, Decl(inferenceUnionArrayDepth.ts, 4, 47))
+
+const result1: Value = flat(n); // Should infer T = Value, not T = Value[]
+>result1 : Symbol(result1, Decl(inferenceUnionArrayDepth.ts, 9, 5))
+>Value : Symbol(Value, Decl(inferenceUnionArrayDepth.ts, 4, 47))
+>flat : Symbol(flat, Decl(inferenceUnionArrayDepth.ts, 0, 0))
+>n : Symbol(n, Decl(inferenceUnionArrayDepth.ts, 8, 13))
+
+// Case 2: Object type (issue #3370)
+type TG = { a: string };
+>TG : Symbol(TG, Decl(inferenceUnionArrayDepth.ts, 9, 31))
+>a : Symbol(a, Decl(inferenceUnionArrayDepth.ts, 12, 11))
+
+function isNestedArray<T>(arr: T[] | T[][]): arr is T[][] {
+>isNestedArray : Symbol(isNestedArray, Decl(inferenceUnionArrayDepth.ts, 12, 24))
+>T : Symbol(T, Decl(inferenceUnionArrayDepth.ts, 14, 23))
+>arr : Symbol(arr, Decl(inferenceUnionArrayDepth.ts, 14, 26))
+>T : Symbol(T, Decl(inferenceUnionArrayDepth.ts, 14, 23))
+>T : Symbol(T, Decl(inferenceUnionArrayDepth.ts, 14, 23))
+>arr : Symbol(arr, Decl(inferenceUnionArrayDepth.ts, 14, 26))
+>T : Symbol(T, Decl(inferenceUnionArrayDepth.ts, 14, 23))
+
+    return Array.isArray(arr) && Array.isArray(arr[0]);
+>Array.isArray : Symbol(ArrayConstructor.isArray, Decl(lib.es5.d.ts, --, --))
+>Array : Symbol(Array, Decl(lib.es5.d.ts, --, --), Decl(lib.es5.d.ts, --, --), Decl(lib.es2015.core.d.ts, --, --), Decl(lib.es2015.iterable.d.ts, --, --), Decl(lib.es2015.symbol.wellknown.d.ts, --, --) ... and 4 more)
+>isArray : Symbol(ArrayConstructor.isArray, Decl(lib.es5.d.ts, --, --))
+>arr : Symbol(arr, Decl(inferenceUnionArrayDepth.ts, 14, 26))
+>Array.isArray : Symbol(ArrayConstructor.isArray, Decl(lib.es5.d.ts, --, --))
+>Array : Symbol(Array, Decl(lib.es5.d.ts, --, --), Decl(lib.es5.d.ts, --, --), Decl(lib.es2015.core.d.ts, --, --), Decl(lib.es2015.iterable.d.ts, --, --), Decl(lib.es2015.symbol.wellknown.d.ts, --, --) ... and 4 more)
+>isArray : Symbol(ArrayConstructor.isArray, Decl(lib.es5.d.ts, --, --))
+>arr : Symbol(arr, Decl(inferenceUnionArrayDepth.ts, 14, 26))
+}
+
+function convert(controls: TG[] | TG[][]): TG[][] {
+>convert : Symbol(convert, Decl(inferenceUnionArrayDepth.ts, 16, 1))
+>controls : Symbol(controls, Decl(inferenceUnionArrayDepth.ts, 18, 17))
+>TG : Symbol(TG, Decl(inferenceUnionArrayDepth.ts, 9, 31))
+>TG : Symbol(TG, Decl(inferenceUnionArrayDepth.ts, 9, 31))
+>TG : Symbol(TG, Decl(inferenceUnionArrayDepth.ts, 9, 31))
+
+    if (isNestedArray(controls)) {
+>isNestedArray : Symbol(isNestedArray, Decl(inferenceUnionArrayDepth.ts, 12, 24))
+>controls : Symbol(controls, Decl(inferenceUnionArrayDepth.ts, 18, 17))
+
+        return controls;
+>controls : Symbol(controls, Decl(inferenceUnionArrayDepth.ts, 18, 17))
+
+    } else {
+        return [controls];
+>controls : Symbol(controls, Decl(inferenceUnionArrayDepth.ts, 18, 17))
+    }
+}
+
+// Case 3: Primitive type (should already work)
+declare const s: string[] | string[][];
+>s : Symbol(s, Decl(inferenceUnionArrayDepth.ts, 27, 13))
+
+const result3: string = flat(s);
+>result3 : Symbol(result3, Decl(inferenceUnionArrayDepth.ts, 28, 5))
+>flat : Symbol(flat, Decl(inferenceUnionArrayDepth.ts, 0, 0))
+>s : Symbol(s, Decl(inferenceUnionArrayDepth.ts, 27, 13))
+
diff --git a/testdata/baselines/reference/compiler/inferenceUnionArrayDepth.types b/testdata/baselines/reference/compiler/inferenceUnionArrayDepth.types
new file mode 100644
index 00000000000..9de13191f56
--- /dev/null
+++ b/testdata/baselines/reference/compiler/inferenceUnionArrayDepth.types
@@ -0,0 +1,78 @@
+//// [tests/cases/compiler/inferenceUnionArrayDepth.ts] ////
+
+=== inferenceUnionArrayDepth.ts ===
+// Regression test for https://github.com/microsoft/typescript-go/issues/1789
+// and https://github.com/microsoft/typescript-go/issues/3370
+// Inference should correctly infer T from T[] | T[][] union parameters.
+
+declare function flat<T>(args: T[] | T[][]): T;
+>flat : <T>(args: T[] | T[][]) => T
+>args : T[] | T[][]
+
+// Case 1: Union type (issue #1789)
+type Value = 1 | 2;
+>Value : Value
+
+declare const n: Value[] | Value[][];
+>n : Value[][] | Value[]
+
+const result1: Value = flat(n); // Should infer T = Value, not T = Value[]
+>result1 : Value
+>flat(n) : Value
+>flat : <T>(args: T[] | T[][]) => T
+>n : Value[][] | Value[]
+
+// Case 2: Object type (issue #3370)
+type TG = { a: string };
+>TG : TG
+>a : string
+
+function isNestedArray<T>(arr: T[] | T[][]): arr is T[][] {
+>isNestedArray : <T>(arr: T[] | T[][]) => arr is T[][]
+>arr : T[] | T[][]
+
+    return Array.isArray(arr) && Array.isArray(arr[0]);
+>Array.isArray(arr) && Array.isArray(arr[0]) : boolean
+>Array.isArray(arr) : boolean
+>Array.isArray : (arg: any) => arg is any[]
+>Array : ArrayConstructor
+>isArray : (arg: any) => arg is any[]
+>arr : T[] | T[][]
+>Array.isArray(arr[0]) : boolean
+>Array.isArray : (arg: any) => arg is any[]
+>Array : ArrayConstructor
+>isArray : (arg: any) => arg is any[]
+>arr[0] : T | T[]
+>arr : T[] | T[][]
+>0 : 0
+}
+
+function convert(controls: TG[] | TG[][]): TG[][] {
+>convert : (controls: TG[] | TG[][]) => TG[][]
+>controls : TG[][] | TG[]
+
+    if (isNestedArray(controls)) {
+>isNestedArray(controls) : boolean
+>isNestedArray : <T>(arr: T[] | T[][]) => arr is T[][]
+>controls : TG[][] | TG[]
+
+        return controls;
+>controls : TG[][]
+
+    } else {
+        return [controls];
+>[controls] : TG[][]
+>controls : TG[]
+    }
+}
+
+// Case 3: Primitive type (should already work)
+declare const s: string[] | string[][];
+>s : string[] | string[][]
+
+const result3: string = flat(s);
+>result3 : string
+>flat(s) : string
+>flat : <T>(args: T[] | T[][]) => T
+>s : string[] | string[][]
+
diff --git a/testdata/tests/cases/compiler/inferenceUnionArrayDepth.ts b/testdata/tests/cases/compiler/inferenceUnionArrayDepth.ts
new file mode 100644
index 00000000000..f7cc31b43c9
--- /dev/null
+++ b/testdata/tests/cases/compiler/inferenceUnionArrayDepth.ts
@@ -0,0 +1,31 @@
+// @strict: true
+
+// Regression test for https://github.com/microsoft/typescript-go/issues/1789
+// and https://github.com/microsoft/typescript-go/issues/3370
+// Inference should correctly infer T from T[] | T[][] union parameters.
+
+declare function flat<T>(args: T[] | T[][]): T;
+
+// Case 1: Union type (issue #1789)
+type Value = 1 | 2;
+declare const n: Value[] | Value[][];
+const result1: Value = flat(n); // Should infer T = Value, not T = Value[]
+
+// Case 2: Object type (issue #3370)
+type TG = { a: string };
+
+function isNestedArray<T>(arr: T[] | T[][]): arr is T[][] {
+    return Array.isArray(arr) && Array.isArray(arr[0]);
+}
+
+function convert(controls: TG[] | TG[][]): TG[][] {
+    if (isNestedArray(controls)) {
+        return controls;
+    } else {
+        return [controls];
+    }
+}
+
+// Case 3: Primitive type (should already work)
+declare const s: string[] | string[][];
+const result3: string = flat(s);