diff --git a/Cargo.lock b/Cargo.lock
index 2a7f7d35..f946eca2 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -31,6 +31,12 @@ dependencies = [
  "memchr",
 ]
 
+[[package]]
+name = "allocator-api2"
+version = "0.2.21"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "683d7910e743518b0e34f1186f92494becacb047c7b6bf616c96772180fef923"
+
 [[package]]
 name = "anstream"
 version = "1.0.0"
@@ -81,12 +87,6 @@ dependencies = [
  "windows-sys 0.61.2",
 ]
 
-[[package]]
-name = "anyhow"
-version = "1.0.104"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "330a5ed07fa54e4702c9d6c4174f74427fc0ef6e214bbd677ae50a5099946470"
-
 [[package]]
 name = "arboard"
 version = "3.7.0"
@@ -145,18 +145,18 @@ checksum = "ac07cdecf99051d9a5238b80f35af32cdeba5b336e55d957b318b50137e18da5"
 
 [[package]]
 name = "bit-set"
-version = "0.5.3"
+version = "0.8.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "0700ddab506f33b20a03b13996eccd309a48e5ff77d0d95926aa0210fb4e95f1"
+checksum = "08807e080ed7f9d5433fa9b275196cfc35414f66a0c79d864dc51a0d825231a3"
 dependencies = [
  "bit-vec",
 ]
 
 [[package]]
 name = "bit-vec"
-version = "0.6.3"
+version = "0.8.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "349f9b6a179ed607305526ca489b34ad0a41aed5f7980fa90eb03160b69598fb"
+checksum = "5e764a1d40d510daf35e07be9eb06e75770908c27d411ee6c92109c9840eaaf7"
 
 [[package]]
 name = "bitflags"
@@ -179,6 +179,12 @@ dependencies = [
  "generic-array",
 ]
 
+[[package]]
+name = "borrow-or-share"
+version = "0.2.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "dc0b364ead1874514c8c2855ab558056ebfeb775653e7ae45ff72f28f8f3166c"
+
 [[package]]
 name = "bumpalo"
 version = "3.20.3"
@@ -385,6 +391,12 @@ dependencies = [
  "typenum",
 ]
 
+[[package]]
+name = "data-encoding"
+version = "2.11.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "4583a4551df46e2792f82ceeac45e850d2e2d5debba0b91f102385cda5b11f06"
+
 [[package]]
 name = "deranged"
 version = "0.5.8"
@@ -426,6 +438,15 @@ dependencies = [
  "syn 3.0.6",
 ]
 
+[[package]]
+name = "email_address"
+version = "0.2.9"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e079f19b08ca6239f47f8ba8509c11cf3ea30095831f7fed61441475edd8c449"
+dependencies = [
+ "serde",
+]
+
 [[package]]
 name = "encode_unicode"
 version = "1.0.0"
@@ -456,9 +477,9 @@ checksum = "0b5343afd4a8365a643ac588dab4cf234a190c7f6c88c9f6dd6ffe00837661b7"
 
 [[package]]
 name = "fancy-regex"
-version = "0.13.0"
+version = "0.19.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "531e46835a22af56d1e3b66f04844bed63158bc094a628bec1d321d9b4c44bf2"
+checksum = "d301f5bf187b3c295fce6468d3875037a0bccc5f6b151c63cac2f85babf21912"
 dependencies = [
  "bit-set",
  "regex-automata",
@@ -507,12 +528,29 @@ dependencies = [
  "bitflags 1.3.2",
 ]
 
+[[package]]
+name = "fluent-uri"
+version = "0.4.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "bc74ac4d8359ae70623506d512209619e5cf8f347124910440dbc221714b328e"
+dependencies = [
+ "borrow-or-share",
+ "ref-cast",
+ "serde",
+]
+
 [[package]]
 name = "fnv"
 version = "1.0.7"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "3f9eec918d3f24069decb9af1554cad7c880e2da24a9afd88aca000531ab82c1"
 
+[[package]]
+name = "foldhash"
+version = "0.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "77ce24cb58228fbb8aa041425bb1050850ac19177686ea6e0f41a70416f56fdb"
+
 [[package]]
 name = "form_urlencoded"
 version = "1.2.2"
@@ -524,12 +562,12 @@ dependencies = [
 
 [[package]]
 name = "fraction"
-version = "0.15.4"
+version = "0.17.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e076045bb43dac435333ed5f04caf35c7463631d0dae2deb2638d94dd0a5b872"
+checksum = "e246562084dde8ebbcc943b261c406ce4f68e5032ec28029a251a47d6a295500"
 dependencies = [
- "lazy_static",
  "num",
+ "num-bigint",
 ]
 
 [[package]]
@@ -621,9 +659,11 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "899def5c37c4fd7b2664648c28120ecec138e4d395b459e5ca34f9cce2dd77fd"
 dependencies = [
  "cfg-if",
+ "js-sys",
  "libc",
  "r-efi 5.3.0",
  "wasip2",
+ "wasm-bindgen",
 ]
 
 [[package]]
@@ -664,6 +704,11 @@ name = "hashbrown"
 version = "0.17.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "ed5909b6e89a2db4456e54cd5f673791d7eca6732202bbf2a9cc504fe2f9b84a"
+dependencies = [
+ "allocator-api2",
+ "equivalent",
+ "foldhash",
+]
 
 [[package]]
 name = "hdrhistogram"
@@ -964,15 +1009,6 @@ version = "1.70.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "a6cb138bb79a146c1bd460005623e142ef0181e3d0219cb493e02f7d08a35695"
 
-[[package]]
-name = "iso8601"
-version = "0.6.6"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4ffd3254cf2b0fc53e38414bdba99719f3e269db8a6519731b68a3a90040c41b"
-dependencies = [
- "nom",
-]
-
 [[package]]
 name = "itoa"
 version = "1.0.18"
@@ -992,39 +1028,56 @@ dependencies = [
 
 [[package]]
 name = "jsonschema"
-version = "0.18.3"
+version = "0.58.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "fa0f4bea31643be4c6a678e9aa4ae44f0db9e5609d5ca9dc9083d06eb3e9a27a"
+checksum = "f622c574a29fb3034a0a90645afee194dfedc75fc124228801b6e77041075bd1"
 dependencies = [
  "ahash",
- "anyhow",
- "base64 0.22.1",
  "bytecount",
- "clap",
+ "data-encoding",
+ "email_address",
  "fancy-regex",
  "fraction",
- "getrandom 0.2.17",
- "iso8601",
+ "getrandom 0.3.4",
  "itoa",
- "memchr",
+ "jsonschema-regex",
+ "jsonschema-value",
  "num-cmp",
- "once_cell",
- "parking_lot",
+ "num-traits",
  "percent-encoding",
+ "referencing",
  "regex",
- "reqwest",
  "serde",
  "serde_json",
- "time",
- "url",
- "uuid",
+ "strum",
+ "unicode-general-category",
+ "uuid-simd",
 ]
 
 [[package]]
-name = "lazy_static"
-version = "1.5.1"
+name = "jsonschema-regex"
+version = "0.58.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "20870f649af7073d53e38067b2a84312175d56ea15217e1b15bc83506ec50afb"
+checksum = "a968fffd387b2ab005bf00c1851f5d26e90df05b6f7ad609ed0d620033cca5e7"
+dependencies = [
+ "regex-syntax",
+]
+
+[[package]]
+name = "jsonschema-value"
+version = "0.58.6"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "39b7670345e5ce87371339d13705dbb9276b7e3e934bbe1efa2c6734a1f65a96"
+dependencies = [
+ "ahash",
+ "bytecount",
+ "fraction",
+ "getrandom 0.3.4",
+ "num-cmp",
+ "num-traits",
+ "serde_json",
+ "zmij",
+]
 
 [[package]]
 name = "libc"
@@ -1078,7 +1131,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "53353550a17c04ac46c585feb189c2db82154fc84b79c7a66c96c2c644f66071"
 dependencies = [
  "bitflags 1.3.2",
- "fluent-uri",
+ "fluent-uri 0.1.4",
  "serde",
  "serde_json",
  "serde_repr",
@@ -1090,6 +1143,12 @@ version = "2.8.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "cf8baf1c55e62ffcace7a9f06f4bd9cd3f0c4beb022d3b367256b91b87513d98"
 
+[[package]]
+name = "micromap"
+version = "0.3.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "c2a86d3146ed3995b5913c414f6664344b9617457320782e64f0bb44afd49d74"
+
 [[package]]
 name = "miniz_oxide"
 version = "0.9.1"
@@ -1111,15 +1170,6 @@ dependencies = [
  "windows-sys 0.61.2",
 ]
 
-[[package]]
-name = "nom"
-version = "8.0.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "df9761775871bdef83bee530e60050f7e54b1105350d6884eb0fb4f46c2f9405"
-dependencies = [
- "memchr",
-]
-
 [[package]]
 name = "num"
 version = "0.4.3"
@@ -1305,6 +1355,12 @@ dependencies = [
  "windows-sys 0.61.2",
 ]
 
+[[package]]
+name = "outref"
+version = "0.5.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "1a80800c0488c3a21695ea981a54918fbb37abf04f4d0720c453632255e2ff0e"
+
 [[package]]
 name = "parking_lot"
 version = "0.12.5"
@@ -1500,6 +1556,43 @@ dependencies = [
  "bitflags 2.13.2",
 ]
 
+[[package]]
+name = "ref-cast"
+version = "1.0.27"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7e440fb4e4b4147295338efb76001ab9e4efc0e5839df2c47fc5ac2381d365c3"
+dependencies = [
+ "ref-cast-impl",
+]
+
+[[package]]
+name = "ref-cast-impl"
+version = "1.0.27"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "92ecd8964f8453721699a1ed72037b0db49ce2f5a5138486ee89bed6f67cdf3a"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn 3.0.6",
+]
+
+[[package]]
+name = "referencing"
+version = "0.58.6"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "558f3855529c0a7e78a48e409fa653456e55f1b167eab4109c16a255b7727e3f"
+dependencies = [
+ "ahash",
+ "fluent-uri 0.4.1",
+ "getrandom 0.3.4",
+ "hashbrown",
+ "itoa",
+ "micromap",
+ "parking_lot",
+ "percent-encoding",
+ "serde_json",
+]
+
 [[package]]
 name = "regex"
 version = "1.13.1"
@@ -1835,6 +1928,27 @@ version = "0.11.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "7da8b5736845d9f2fcb837ea5d9e2628564b3b043a70948a3f0b778838c5fb4f"
 
+[[package]]
+name = "strum"
+version = "0.28.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9628de9b8791db39ceda2b119bbe13134770b56c138ec1d3af810d045c04f9bd"
+dependencies = [
+ "strum_macros",
+]
+
+[[package]]
+name = "strum_macros"
+version = "0.28.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "ab85eea0270ee17587ed4156089e10b9e6880ee688791d45a905f5b1ca36f664"
+dependencies = [
+ "heck",
+ "proc-macro2",
+ "quote",
+ "syn 2.0.119",
+]
+
 [[package]]
 name = "subtle"
 version = "2.6.1"
@@ -2100,6 +2214,12 @@ version = "1.20.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "b6f5e870be6c3b371b77fe0ee0bafb859fa4964b4404c27de1d380043c4dda20"
 
+[[package]]
+name = "unicode-general-category"
+version = "1.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "0b993bddc193ae5bd0d623b49ec06ac3e9312875fdae725a975c51db1cc1677f"
+
 [[package]]
 name = "unicode-ident"
 version = "1.0.26"
@@ -2146,13 +2266,13 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "06abde3611657adf66d383f00b093d7faecc7fa57071cce2578660c9f1010821"
 
 [[package]]
-name = "uuid"
-version = "1.26.1"
+name = "uuid-simd"
+version = "0.8.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "2ef6dac1e96601b4fb3acccccff2139741fcb757cb9a36089bf5be91cfb285ce"
+checksum = "23b082222b4f6619906941c17eb2297fff4c2fb96cb60164170522942a200bd8"
 dependencies = [
- "js-sys",
- "wasm-bindgen",
+ "outref",
+ "vsimd",
 ]
 
 [[package]]
@@ -2161,6 +2281,12 @@ version = "0.9.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "0b928f33d975fc6ad9f86c8f283853ad26bdd5b10b7f1542aa2fa15e2289105a"
 
+[[package]]
+name = "vsimd"
+version = "0.8.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5c3082ca00d5a5ef149bb8b555a72ae84c9c59f7250f013ac822ac2e49b19c64"
+
 [[package]]
 name = "want"
 version = "0.3.2"
diff --git a/crates/wright-cli/Cargo.toml b/crates/wright-cli/Cargo.toml
index 102d441d..4d479977 100644
--- a/crates/wright-cli/Cargo.toml
+++ b/crates/wright-cli/Cargo.toml
@@ -36,7 +36,7 @@ tiny_http = { version = "0.12", optional = true }
 
 [dev-dependencies]
 insta = { version = "1", features = ["json"] }
-jsonschema = "0.18"
+jsonschema = { version = "0.58", default-features = false }
 sha2.workspace = true
 wright-analyzer.workspace = true
 workshop-rs.workspace = true
diff --git a/crates/wright-cli/tests/agent_contract.rs b/crates/wright-cli/tests/agent_contract.rs
index 6a83da62..14e8abc8 100644
--- a/crates/wright-cli/tests/agent_contract.rs
+++ b/crates/wright-cli/tests/agent_contract.rs
@@ -3,7 +3,7 @@ use std::io::Write;
 use std::path::{Path, PathBuf};
 use std::process::{Command, Stdio};
 
-use jsonschema::JSONSchema;
+use jsonschema::validator_for;
 use serde_json::{Value, json};
 use wright_driver::service::{AGENT_CONTRACT, ToolRequest, ToolResponse, ToolService};
 use wright_driver::{CompilerSession, FindingSelection, InputSpec, SessionConfig, SourceKind};
@@ -211,19 +211,17 @@ fn agent_v1_schema_covers_every_advertised_request_and_response() {
         &std::fs::read_to_string(root.join("schemas/wright-agent-v1.schema.json")).unwrap(),
     )
     .unwrap();
-    let request_schema = JSONSchema::compile(&schema).expect("request schema compiles");
+    let request_schema = validator_for(&schema).expect("request schema compiles");
     let mut response_document = schema.clone();
     response_document["$ref"] = Value::String("#/$defs/ToolResponse".to_string());
-    let response_schema =
-        JSONSchema::compile(&response_document).expect("response schema compiles");
+    let response_schema = validator_for(&response_document).expect("response schema compiles");
     let mut capabilities_document = schema.clone();
     capabilities_document["$ref"] = Value::String("#/$defs/Capabilities".to_string());
     let capabilities_schema =
-        JSONSchema::compile(&capabilities_document).expect("capability schema compiles");
+        validator_for(&capabilities_document).expect("capability schema compiles");
     let mut edit_range_document = schema.clone();
     edit_range_document["$ref"] = Value::String("#/$defs/EditRange".to_string());
-    let edit_range_schema =
-        JSONSchema::compile(&edit_range_document).expect("range schema compiles");
+    let edit_range_schema = validator_for(&edit_range_document).expect("range schema compiles");
 
     assert_eq!(AGENT_CONTRACT, "wright-agent/v1");
     assert_eq!(
@@ -392,7 +390,7 @@ fn agent_v1_schema_covers_every_advertised_request_and_response() {
         let mut operation_document = schema.clone();
         operation_document["$ref"] = Value::String(reference.to_string());
         let operation_schema =
-            JSONSchema::compile(&operation_document).expect("operation result schema compiles");
+            validator_for(&operation_document).expect("operation result schema compiles");
         assert!(
             operation_schema.is_valid(result),
             "{operation} result does not match {reference}: {result}"
@@ -422,7 +420,7 @@ fn agent_v1_schema_covers_every_advertised_request_and_response() {
         let mut operation_document = schema.clone();
         operation_document["$ref"] = Value::String(reference.to_string());
         let operation_schema =
-            JSONSchema::compile(&operation_document).expect("operation result schema compiles");
+            validator_for(&operation_document).expect("operation result schema compiles");
         assert!(
             operation_schema.is_valid(&result),
             "{} all result does not match {reference}: {result}",
@@ -692,7 +690,7 @@ fn rule_content_conforms_to_the_owner_schema() {
     };
     let owner: Value =
         serde_json::from_str(workshop_rs::rules::content::RULE_CONTENT_V1_SCHEMA).unwrap();
-    let owner = JSONSchema::compile(&owner).expect("owner schema compiles");
+    let owner = validator_for(&owner).expect("owner schema compiles");
     let wright: Value = serde_json::from_str(
         &std::fs::read_to_string(workspace_root().join("schemas/wright-agent-v1.schema.json"))
             .unwrap(),
@@ -700,7 +698,7 @@ fn rule_content_conforms_to_the_owner_schema() {
     .unwrap();
     let mut response = wright.clone();
     response["$ref"] = json!("#/$defs/RulesResult");
-    let response = JSONSchema::compile(&response).expect("response schema compiles");
+    let response = validator_for(&response).expect("response schema compiles");
     assert!(response.is_valid(&result), "{result}");
     for rule in result["rules"].as_array().unwrap() {
         // Wright adds `span` to each statement; the owner's document has none.
diff --git a/crates/wright-cli/tests/agent_contract_vocabulary.rs b/crates/wright-cli/tests/agent_contract_vocabulary.rs
index 432056eb..087b3cd1 100644
--- a/crates/wright-cli/tests/agent_contract_vocabulary.rs
+++ b/crates/wright-cli/tests/agent_contract_vocabulary.rs
@@ -3,7 +3,7 @@
 
 use std::path::{Path, PathBuf};
 
-use jsonschema::JSONSchema;
+use jsonschema::validator_for;
 use serde_json::{Value, json};
 use wright_driver::service::{ToolRequest, ToolResponse, ToolService};
 use wright_driver::{CompilerSession, InputSpec, SessionConfig, SourceKind};
@@ -36,7 +36,7 @@ fn lookup_result_schema_covers_callable_returns_and_variadic() {
     .unwrap();
     let mut document = schema.clone();
     document["$ref"] = Value::String("#/$defs/LookupResult".to_string());
-    let result_schema = JSONSchema::compile(&document).expect("result schema compiles");
+    let result_schema = validator_for(&document).expect("result schema compiles");
 
     let ToolResponse::Ok { result } = service_response(&ToolRequest::Lookup {
         language: "workshop".to_string(),
@@ -73,7 +73,7 @@ fn list_entries_request_and_result_validate_against_the_committed_schema() {
     .unwrap();
     let mut request = schema.clone();
     request["$ref"] = Value::String("#/$defs/ListEntriesRequest".to_string());
-    let request_schema = JSONSchema::compile(&request).expect("request schema compiles");
+    let request_schema = validator_for(&request).expect("request schema compiles");
     let valid = json!({"op":"listEntries","language":"workshop","kind":"enumMember","within":"Hero","pageSize":500,"cursor":"a.b"});
     assert!(request_schema.is_valid(&valid));
     for invalid in [
@@ -88,7 +88,7 @@ fn list_entries_request_and_result_validate_against_the_committed_schema() {
 
     let mut result_document = schema.clone();
     result_document["$ref"] = Value::String("#/$defs/ListEntriesResult".to_string());
-    let result_schema = JSONSchema::compile(&result_document).expect("result schema compiles");
+    let result_schema = validator_for(&result_document).expect("result schema compiles");
     let ToolResponse::Ok { result } = service_response(&ToolRequest::ListEntries {
         language: "workshop".to_string(),
         kind: "action".to_string(),
diff --git a/crates/wright-cli/tests/diagnostics_schema.rs b/crates/wright-cli/tests/diagnostics_schema.rs
index 44ab61e1..a742ae22 100644
--- a/crates/wright-cli/tests/diagnostics_schema.rs
+++ b/crates/wright-cli/tests/diagnostics_schema.rs
@@ -69,9 +69,12 @@ fn check_json_matches_schema_and_snapshot() {
 
 fn validate_output(schema: &serde_json::Value, output: &[u8]) -> serde_json::Value {
     let value: serde_json::Value = serde_json::from_slice(output).expect("JSON output");
-    let validator = jsonschema::JSONSchema::compile(schema).expect("schema compiles");
-    if let Err(errors) = validator.validate(&value) {
-        let errors = errors.map(|error| error.to_string()).collect::<Vec<_>>();
+    let validator = jsonschema::validator_for(schema).expect("schema compiles");
+    let errors = validator
+        .iter_errors(&value)
+        .map(|error| error.to_string())
+        .collect::<Vec<_>>();
+    if !errors.is_empty() {
         panic!("check output does not validate: {errors:?}");
     }
     value