diff --git a/pkg/tfbridge/typechecker/typechecker.go b/pkg/tfbridge/typechecker/typechecker.go
index c84cbb7a7..2f8b47d78 100644
--- a/pkg/tfbridge/typechecker/typechecker.go
+++ b/pkg/tfbridge/typechecker/typechecker.go
@@ -161,7 +161,16 @@ func (v *TypeChecker) validatePropertyValue(
 
 	switch typeSpec.Type {
 	case "boolean":
-		if !propertyValue.IsBool() {
+		// Check for strings that are values "true" or "false".
+		//TODO: Remove the boolString condition when https://github.com/pulumi/pulumi-terraform-bridge/issues/2520
+		// is resolved. This is a workaround for the config encoding not honoring type overrides.
+		var boolString bool
+		if propertyValue.IsString() {
+			if propertyValue.StringValue() == "true" || propertyValue.StringValue() == "false" {
+				boolString = true
+			}
+		}
+		if !propertyValue.IsBool() && !boolString {
 			return []Failure{newTypeFailure(propertyPath, typeSpec.Type, propertyValue)}
 		}
 		return nil
diff --git a/pkg/tfbridge/typechecker/typechecker_test.go b/pkg/tfbridge/typechecker/typechecker_test.go
index a8007a3ad..e2bfbff0f 100644
--- a/pkg/tfbridge/typechecker/typechecker_test.go
+++ b/pkg/tfbridge/typechecker/typechecker_test.go
@@ -1631,6 +1631,14 @@ func TestValidateConfigType(t *testing.T) {
 				})),
 			}),
 		},
+		{
+			//TODO: Remove this test when https://github.com/pulumi/pulumi-terraform-bridge/issues/2520 is resolved.
+			// This tests a workaround path to keep the type checker from tripping on missing functionality in the
+			// config encoding and will fail once that is fixed.
+			name:      "allows_bool_strings",
+			inputName: "skipMetadataApiCheck",
+			input:     resource.PropertyValue{V: "true"},
+		},
 	}
 	for _, tc := range testCases {
 		tc := tc
@@ -1661,6 +1669,11 @@ func TestValidateConfigType(t *testing.T) {
 								},
 							},
 						},
+						"skipMetadataApiCheck": {
+							TypeSpec: pschema.TypeSpec{
+								Type: "boolean",
+							},
+						},
 					},
 				},
 			}