diff --git a/output-tests/draft2019-09/structure/basic.json b/output-tests/draft2019-09/structure/basic.json
new file mode 100644
index 00000000..1303272e
--- /dev/null
+++ b/output-tests/draft2019-09/structure/basic.json
@@ -0,0 +1,53 @@
+[
+    {
+        "description": "basic output has valid, errors array, each error has keywordLocation, instanceLocation, valid",
+        "schema": {
+            "$schema": "https://json-schema.org/draft/2019-09/schema",
+            "$id": "https://json-schema.org/tests/structure/draft2019-09/basic/0",
+            "type": "string",
+            "anyOf": [true]
+        },
+        "tests": [
+            {
+                "description": "invalid data produces valid: false and errors array",
+                "data": 1,
+                "output": {
+                    "basic": {
+                        "$id": "https://json-schema.org/tests/structure/draft2019-09/basic/0/tests/0/basic",
+                        "$ref": "/draft/2019-09/output/schema",
+                        "properties": {
+                            "valid": { "const": false },
+                            "errors": {
+                                "type": "array",
+                                "minItems": 1,
+                                "items": {
+                                    "required": ["keywordLocation", "instanceLocation", "valid"],
+                                    "properties": {
+                                        "keywordLocation": { "type": "string" },
+                                        "instanceLocation": { "type": "string" },
+                                        "valid": { "type": "boolean" }
+                                    }
+                                }
+                            }
+                        },
+                        "required": ["valid", "errors"]
+                    }
+                }
+            },
+            {
+                "description": "valid data produces valid true, no errors or empty",
+                "data": "hello",
+                "output": {
+                    "basic": {
+                        "$id": "https://json-schema.org/tests/structure/draft2019-09/basic/0/tests/1/basic",
+                        "$ref": "/draft/2019-09/output/schema",
+                        "properties": {
+                            "valid": { "const": true }
+                        },
+                        "required": ["valid"]
+                    }
+                }
+            }
+        ]
+    }
+]
diff --git a/output-tests/draft2019-09/structure/detailed.json b/output-tests/draft2019-09/structure/detailed.json
new file mode 100644
index 00000000..3e1ede99
--- /dev/null
+++ b/output-tests/draft2019-09/structure/detailed.json
@@ -0,0 +1,43 @@
+[
+    {
+        "description": "detailed output has keywordLocation, instanceLocation, valid, nested errors when invalid",
+        "schema": {
+            "$schema": "https://json-schema.org/draft/2019-09/schema",
+            "$id": "https://json-schema.org/tests/structure/draft2019-09/detailed/0",
+            "allOf": [
+                { "type": "string" },
+                { "minLength": 10 }
+            ]
+        },
+        "tests": [
+            {
+                "description": "invalid data produces nested errors with required fields",
+                "data": 1,
+                "output": {
+                    "detailed": {
+                        "$id": "https://json-schema.org/tests/structure/draft2019-09/detailed/0/tests/0/detailed",
+                        "$ref": "/draft/2019-09/output/schema",
+                        "properties": {
+                            "keywordLocation": { "type": "string" },
+                            "instanceLocation": { "type": "string" },
+                            "valid": { "const": false },
+                            "errors": {
+                                "type": "array",
+                                "minItems": 1,
+                                "items": {
+                                    "required": ["keywordLocation", "instanceLocation", "valid"],
+                                    "properties": {
+                                        "keywordLocation": { "type": "string" },
+                                        "instanceLocation": { "type": "string" },
+                                        "valid": { "type": "boolean" }
+                                    }
+                                }
+                            }
+                        },
+                        "required": ["keywordLocation", "instanceLocation", "valid", "errors"]
+                    }
+                }
+            }
+        ]
+    }
+]
diff --git a/output-tests/draft2019-09/structure/flag.json b/output-tests/draft2019-09/structure/flag.json
new file mode 100644
index 00000000..a177bfe0
--- /dev/null
+++ b/output-tests/draft2019-09/structure/flag.json
@@ -0,0 +1,42 @@
+[
+    {
+        "description": "flag output has only valid key, no extra keys",
+        "schema": {
+            "$schema": "https://json-schema.org/draft/2019-09/schema",
+            "$id": "https://json-schema.org/tests/structure/draft2019-09/flag/0",
+            "type": "string"
+        },
+        "tests": [
+            {
+                "description": "valid schema and valid data produces only valid true",
+                "data": "hello",
+                "output": {
+                    "flag": {
+                        "$id": "https://json-schema.org/tests/structure/draft2019-09/flag/0/tests/0/flag",
+                        "$ref": "/draft/2019-09/output/schema",
+                        "properties": {
+                            "valid": { "const": true }
+                        },
+                        "required": ["valid"],
+                        "additionalProperties": false
+                    }
+                }
+            },
+            {
+                "description": "valid schema and invalid data produces only valid false",
+                "data": 1,
+                "output": {
+                    "flag": {
+                        "$id": "https://json-schema.org/tests/structure/draft2019-09/flag/0/tests/1/flag",
+                        "$ref": "/draft/2019-09/output/schema",
+                        "properties": {
+                            "valid": { "const": false }
+                        },
+                        "required": ["valid"],
+                        "additionalProperties": false
+                    }
+                }
+            }
+        ]
+    }
+]
diff --git a/output-tests/draft2019-09/structure/verbose.json b/output-tests/draft2019-09/structure/verbose.json
new file mode 100644
index 00000000..ee75e146
--- /dev/null
+++ b/output-tests/draft2019-09/structure/verbose.json
@@ -0,0 +1,41 @@
+[
+    {
+        "description": "verbose output includes every evaluated keyword, annotations for passing keywords",
+        "schema": {
+            "$schema": "https://json-schema.org/draft/2019-09/schema",
+            "$id": "https://json-schema.org/tests/structure/draft2019-09/verbose/0",
+            "type": "object",
+            "properties": {
+                "name": { "type": "string" }
+            }
+        },
+        "tests": [
+            {
+                "description": "valid data produces annotations for type and properties keywords",
+                "data": { "name": "test" },
+                "output": {
+                    "verbose": {
+                        "$id": "https://json-schema.org/tests/structure/draft2019-09/verbose/0/tests/0/verbose",
+                        "$ref": "/draft/2019-09/output/schema",
+                        "properties": {
+                            "valid": { "const": true },
+                            "annotations": {
+                                "type": "array",
+                                "minItems": 1,
+                                "items": {
+                                    "required": ["keywordLocation", "instanceLocation", "valid"],
+                                    "properties": {
+                                        "keywordLocation": { "type": "string" },
+                                        "instanceLocation": { "type": "string" },
+                                        "valid": { "type": "boolean" }
+                                    }
+                                }
+                            }
+                        },
+                        "required": ["valid", "annotations"]
+                    }
+                }
+            }
+        ]
+    }
+]
diff --git a/output-tests/draft2020-12/structure/basic.json b/output-tests/draft2020-12/structure/basic.json
new file mode 100644
index 00000000..8d1d9909
--- /dev/null
+++ b/output-tests/draft2020-12/structure/basic.json
@@ -0,0 +1,53 @@
+[
+    {
+        "description": "basic output has valid, errors array, each error has keywordLocation, instanceLocation, valid",
+        "schema": {
+            "$schema": "https://json-schema.org/draft/2020-12/schema",
+            "$id": "https://json-schema.org/tests/structure/draft2020-12/basic/0",
+            "type": "string",
+            "anyOf": [true]
+        },
+        "tests": [
+            {
+                "description": "invalid data produces valid: false and errors array",
+                "data": 1,
+                "output": {
+                    "basic": {
+                        "$id": "https://json-schema.org/tests/structure/draft2020-12/basic/0/tests/0/basic",
+                        "$ref": "/draft/2020-12/output/schema",
+                        "properties": {
+                            "valid": { "const": false },
+                            "errors": {
+                                "type": "array",
+                                "minItems": 1,
+                                "items": {
+                                    "required": ["keywordLocation", "instanceLocation", "valid"],
+                                    "properties": {
+                                        "keywordLocation": { "type": "string" },
+                                        "instanceLocation": { "type": "string" },
+                                        "valid": { "type": "boolean" }
+                                    }
+                                }
+                            }
+                        },
+                        "required": ["valid", "errors"]
+                    }
+                }
+            },
+            {
+                "description": "valid data produces valid true, no errors or empty",
+                "data": "hello",
+                "output": {
+                    "basic": {
+                        "$id": "https://json-schema.org/tests/structure/draft2020-12/basic/0/tests/1/basic",
+                        "$ref": "/draft/2020-12/output/schema",
+                        "properties": {
+                            "valid": { "const": true }
+                        },
+                        "required": ["valid"]
+                    }
+                }
+            }
+        ]
+    }
+]
diff --git a/output-tests/draft2020-12/structure/detailed.json b/output-tests/draft2020-12/structure/detailed.json
new file mode 100644
index 00000000..0bf84aa8
--- /dev/null
+++ b/output-tests/draft2020-12/structure/detailed.json
@@ -0,0 +1,43 @@
+[
+    {
+        "description": "detailed output has keywordLocation, instanceLocation, valid, nested errors when invalid",
+        "schema": {
+            "$schema": "https://json-schema.org/draft/2020-12/schema",
+            "$id": "https://json-schema.org/tests/structure/draft2020-12/detailed/0",
+            "allOf": [
+                { "type": "string" },
+                { "minLength": 10 }
+            ]
+        },
+        "tests": [
+            {
+                "description": "invalid data produces nested errors with required fields",
+                "data": 1,
+                "output": {
+                    "detailed": {
+                        "$id": "https://json-schema.org/tests/structure/draft2020-12/detailed/0/tests/0/detailed",
+                        "$ref": "/draft/2020-12/output/schema",
+                        "properties": {
+                            "keywordLocation": { "type": "string" },
+                            "instanceLocation": { "type": "string" },
+                            "valid": { "const": false },
+                            "errors": {
+                                "type": "array",
+                                "minItems": 1,
+                                "items": {
+                                    "required": ["keywordLocation", "instanceLocation", "valid"],
+                                    "properties": {
+                                        "keywordLocation": { "type": "string" },
+                                        "instanceLocation": { "type": "string" },
+                                        "valid": { "type": "boolean" }
+                                    }
+                                }
+                            }
+                        },
+                        "required": ["keywordLocation", "instanceLocation", "valid", "errors"]
+                    }
+                }
+            }
+        ]
+    }
+]
diff --git a/output-tests/draft2020-12/structure/flag.json b/output-tests/draft2020-12/structure/flag.json
new file mode 100644
index 00000000..eaf15b83
--- /dev/null
+++ b/output-tests/draft2020-12/structure/flag.json
@@ -0,0 +1,42 @@
+[
+    {
+        "description": "flag output has only valid key, no extra keys",
+        "schema": {
+            "$schema": "https://json-schema.org/draft/2020-12/schema",
+            "$id": "https://json-schema.org/tests/structure/draft2020-12/flag/0",
+            "type": "string"
+        },
+        "tests": [
+            {
+                "description": "valid schema and valid data produces only valid true",
+                "data": "hello",
+                "output": {
+                    "flag": {
+                        "$id": "https://json-schema.org/tests/structure/draft2020-12/flag/0/tests/0/flag",
+                        "$ref": "/draft/2020-12/output/schema",
+                        "properties": {
+                            "valid": { "const": true }
+                        },
+                        "required": ["valid"],
+                        "additionalProperties": false
+                    }
+                }
+            },
+            {
+                "description": "valid schema and invalid data produces only valid false",
+                "data": 1,
+                "output": {
+                    "flag": {
+                        "$id": "https://json-schema.org/tests/structure/draft2020-12/flag/0/tests/1/flag",
+                        "$ref": "/draft/2020-12/output/schema",
+                        "properties": {
+                            "valid": { "const": false }
+                        },
+                        "required": ["valid"],
+                        "additionalProperties": false
+                    }
+                }
+            }
+        ]
+    }
+]
diff --git a/output-tests/draft2020-12/structure/verbose.json b/output-tests/draft2020-12/structure/verbose.json
new file mode 100644
index 00000000..4cdc2409
--- /dev/null
+++ b/output-tests/draft2020-12/structure/verbose.json
@@ -0,0 +1,41 @@
+[
+    {
+        "description": "verbose output includes every evaluated keyword, annotations for passing keywords",
+        "schema": {
+            "$schema": "https://json-schema.org/draft/2020-12/schema",
+            "$id": "https://json-schema.org/tests/structure/draft2020-12/verbose/0",
+            "type": "object",
+            "properties": {
+                "name": { "type": "string" }
+            }
+        },
+        "tests": [
+            {
+                "description": "valid data produces annotations for type and properties keywords",
+                "data": { "name": "test" },
+                "output": {
+                    "verbose": {
+                        "$id": "https://json-schema.org/tests/structure/draft2020-12/verbose/0/tests/0/verbose",
+                        "$ref": "/draft/2020-12/output/schema",
+                        "properties": {
+                            "valid": { "const": true },
+                            "annotations": {
+                                "type": "array",
+                                "minItems": 1,
+                                "items": {
+                                    "required": ["keywordLocation", "instanceLocation", "valid"],
+                                    "properties": {
+                                        "keywordLocation": { "type": "string" },
+                                        "instanceLocation": { "type": "string" },
+                                        "valid": { "type": "boolean" }
+                                    }
+                                }
+                            }
+                        },
+                        "required": ["valid", "annotations"]
+                    }
+                }
+            }
+        ]
+    }
+]