From 1d1037b912e0fd8e72a0c4e80f02eeb7c700cc82 Mon Sep 17 00:00:00 2001
From: Tony Arcieri <bascule@gmail.com>
Date: Wed, 3 May 2023 18:50:04 -0600
Subject: [PATCH] Initial proptests (#326)

Adds proptests for RSASSA-PKCS1-v1_5.

Includes a commented-out test for RSASSA-PSS which is currently failing.
---
 Cargo.lock         | 334 ++++++++++++++++++++++++++++++++++++++++++++-
 Cargo.toml         |   1 +
 tests/proptests.rs |  42 ++++++
 3 files changed, 375 insertions(+), 2 deletions(-)
 create mode 100644 tests/proptests.rs

diff --git a/Cargo.lock b/Cargo.lock
index 3280c65..2374ad1 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -25,6 +25,27 @@ version = "1.6.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "8c3c1a368f70d6cf7302d78f8f7093da241fb8e8807c05cc9e51a125895a6d5b"
 
+[[package]]
+name = "bit-set"
+version = "0.5.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "0700ddab506f33b20a03b13996eccd309a48e5ff77d0d95926aa0210fb4e95f1"
+dependencies = [
+ "bit-vec",
+]
+
+[[package]]
+name = "bit-vec"
+version = "0.6.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "349f9b6a179ed607305526ca489b34ad0a41aed5f7980fa90eb03160b69598fb"
+
+[[package]]
+name = "bitflags"
+version = "1.3.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "bef38d45163c2f1dde094a7dfd33ccf595c92905c8f8f4fdc18d06fb1037718a"
+
 [[package]]
 name = "block-buffer"
 version = "0.10.3"
@@ -58,6 +79,12 @@ dependencies = [
  "cipher",
 ]
 
+[[package]]
+name = "cc"
+version = "1.0.79"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "50d30906286121d95be3d479533b458f87493b30a4b5f79a607db8f5d11aa91f"
+
 [[package]]
 name = "cfg-if"
 version = "1.0.0"
@@ -122,6 +149,42 @@ dependencies = [
  "subtle",
 ]
 
+[[package]]
+name = "errno"
+version = "0.3.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "4bcfec3a70f97c962c307b2d2c56e358cf1d00b558d74262b5f929ee8cc7e73a"
+dependencies = [
+ "errno-dragonfly",
+ "libc",
+ "windows-sys 0.48.0",
+]
+
+[[package]]
+name = "errno-dragonfly"
+version = "0.1.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "aa68f1b12764fab894d2755d2518754e71b4fd80ecfb822714a1206c2aab39bf"
+dependencies = [
+ "cc",
+ "libc",
+]
+
+[[package]]
+name = "fastrand"
+version = "1.9.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e51093e27b0797c359783294ca4f0a911c270184cb10f85783b118614a1501be"
+dependencies = [
+ "instant",
+]
+
+[[package]]
+name = "fnv"
+version = "1.0.7"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3f9eec918d3f24069decb9af1554cad7c880e2da24a9afd88aca000531ab82c1"
+
 [[package]]
 name = "generic-array"
 version = "0.14.6"
@@ -143,6 +206,12 @@ dependencies = [
  "wasi",
 ]
 
+[[package]]
+name = "hermit-abi"
+version = "0.3.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "fed44880c466736ef9a5c5b5facefb5ed0785676d0c02d612db14e54f0d84286"
+
 [[package]]
 name = "hex-literal"
 version = "0.4.1"
@@ -168,6 +237,26 @@ dependencies = [
  "generic-array",
 ]
 
+[[package]]
+name = "instant"
+version = "0.1.12"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7a5bbe824c507c5da5956355e86a746d82e0e1464f65d862cc5e71da70e94b2c"
+dependencies = [
+ "cfg-if",
+]
+
+[[package]]
+name = "io-lifetimes"
+version = "1.0.10"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9c66c74d2ae7e79a5a8f7ac924adbe38ee42a859c6539ad869eb51f0b52dc220"
+dependencies = [
+ "hermit-abi",
+ "libc",
+ "windows-sys 0.48.0",
+]
+
 [[package]]
 name = "keccak"
 version = "0.1.3"
@@ -188,9 +277,9 @@ dependencies = [
 
 [[package]]
 name = "libc"
-version = "0.2.139"
+version = "0.2.142"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "201de327520df007757c1f0adce6e827fe8562fbc28bfd9c15571c66ca1f5f79"
+checksum = "6a987beff54b60ffa6d51982e1aa1146bc42f19bd26be28b0586f252fccf5317"
 
 [[package]]
 name = "libm"
@@ -198,6 +287,12 @@ version = "0.2.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "348108ab3fba42ec82ff6e9564fc4ca0247bdccdc68dd8af9764bbc79c3c8ffb"
 
+[[package]]
+name = "linux-raw-sys"
+version = "0.3.6"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b64f40e5e03e0d54f03845c8197d0291253cdbedfb1cb46b13c2c117554a9f4c"
+
 [[package]]
 name = "num-bigint-dig"
 version = "0.8.2"
@@ -319,6 +414,39 @@ dependencies = [
  "unicode-ident",
 ]
 
+[[package]]
+name = "proptest"
+version = "1.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "29f1b898011ce9595050a68e60f90bad083ff2987a695a42357134c8381fba70"
+dependencies = [
+ "bit-set",
+ "bitflags",
+ "byteorder",
+ "lazy_static",
+ "num-traits",
+ "quick-error 2.0.1",
+ "rand",
+ "rand_chacha",
+ "rand_xorshift",
+ "regex-syntax",
+ "rusty-fork",
+ "tempfile",
+ "unarray",
+]
+
+[[package]]
+name = "quick-error"
+version = "1.2.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "a1d01941d82fa2ab50be1e79e6714289dd7cde78eba4c074bc5a4374f650dfe0"
+
+[[package]]
+name = "quick-error"
+version = "2.0.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "a993555f31e5a609f617c12db6250dedcac1b0a85076912c436e6fc9b2c8e6a3"
+
 [[package]]
 name = "quote"
 version = "1.0.23"
@@ -367,6 +495,21 @@ dependencies = [
  "rand_core",
 ]
 
+[[package]]
+name = "redox_syscall"
+version = "0.3.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "567664f262709473930a4bf9e51bf2ebf3348f2e748ccc50dea20646858f8f29"
+dependencies = [
+ "bitflags",
+]
+
+[[package]]
+name = "regex-syntax"
+version = "0.6.29"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f162c6dd7b008981e4d40210aca20b4bd0f9b60ca9271061b07f78537722f2e1"
+
 [[package]]
 name = "rsa"
 version = "0.9.0"
@@ -382,6 +525,7 @@ dependencies = [
  "num-traits",
  "pkcs1",
  "pkcs8",
+ "proptest",
  "rand",
  "rand_chacha",
  "rand_core",
@@ -396,6 +540,32 @@ dependencies = [
  "zeroize",
 ]
 
+[[package]]
+name = "rustix"
+version = "0.37.18"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8bbfc1d1c7c40c01715f47d71444744a81669ca84e8b63e25a55e169b1f86433"
+dependencies = [
+ "bitflags",
+ "errno",
+ "io-lifetimes",
+ "libc",
+ "linux-raw-sys",
+ "windows-sys 0.48.0",
+]
+
+[[package]]
+name = "rusty-fork"
+version = "0.3.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "cb3dcc6e454c328bb824492db107ab7c0ae8fcffe4ad210136ef014458c1bc4f"
+dependencies = [
+ "fnv",
+ "quick-error 1.2.3",
+ "tempfile",
+ "wait-timeout",
+]
+
 [[package]]
 name = "salsa20"
 version = "0.10.2"
@@ -526,12 +696,31 @@ dependencies = [
  "unicode-ident",
 ]
 
+[[package]]
+name = "tempfile"
+version = "3.5.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b9fbec84f381d5795b08656e4912bec604d162bff9291d6189a78f4c8ab87998"
+dependencies = [
+ "cfg-if",
+ "fastrand",
+ "redox_syscall",
+ "rustix",
+ "windows-sys 0.45.0",
+]
+
 [[package]]
 name = "typenum"
 version = "1.16.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "497961ef93d974e23eb6f433eb5fe1b7930b659f06d12dec6fc44a8f554c0bba"
 
+[[package]]
+name = "unarray"
+version = "0.1.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "eaea85b334db583fe3274d12b4cd1880032beab409c0d774be044d4480ab9a94"
+
 [[package]]
 name = "unicode-ident"
 version = "1.0.6"
@@ -544,12 +733,153 @@ version = "0.9.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "49874b5167b65d7193b8aba1567f5c7d93d001cafc34600cee003eda787e483f"
 
+[[package]]
+name = "wait-timeout"
+version = "0.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9f200f5b12eb75f8c1ed65abd4b2db8a6e1b138a20de009dacee265a2498f3f6"
+dependencies = [
+ "libc",
+]
+
 [[package]]
 name = "wasi"
 version = "0.11.0+wasi-snapshot-preview1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "9c8d87e72b64a3b4db28d11ce29237c246188f4f51057d65a7eab63b7987e423"
 
+[[package]]
+name = "windows-sys"
+version = "0.45.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "75283be5efb2831d37ea142365f009c02ec203cd29a3ebecbc093d52315b66d0"
+dependencies = [
+ "windows-targets 0.42.2",
+]
+
+[[package]]
+name = "windows-sys"
+version = "0.48.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "677d2418bec65e3338edb076e806bc1ec15693c5d0104683f2efe857f61056a9"
+dependencies = [
+ "windows-targets 0.48.0",
+]
+
+[[package]]
+name = "windows-targets"
+version = "0.42.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8e5180c00cd44c9b1c88adb3693291f1cd93605ded80c250a75d472756b4d071"
+dependencies = [
+ "windows_aarch64_gnullvm 0.42.2",
+ "windows_aarch64_msvc 0.42.2",
+ "windows_i686_gnu 0.42.2",
+ "windows_i686_msvc 0.42.2",
+ "windows_x86_64_gnu 0.42.2",
+ "windows_x86_64_gnullvm 0.42.2",
+ "windows_x86_64_msvc 0.42.2",
+]
+
+[[package]]
+name = "windows-targets"
+version = "0.48.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7b1eb6f0cd7c80c79759c929114ef071b87354ce476d9d94271031c0497adfd5"
+dependencies = [
+ "windows_aarch64_gnullvm 0.48.0",
+ "windows_aarch64_msvc 0.48.0",
+ "windows_i686_gnu 0.48.0",
+ "windows_i686_msvc 0.48.0",
+ "windows_x86_64_gnu 0.48.0",
+ "windows_x86_64_gnullvm 0.48.0",
+ "windows_x86_64_msvc 0.48.0",
+]
+
+[[package]]
+name = "windows_aarch64_gnullvm"
+version = "0.42.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "597a5118570b68bc08d8d59125332c54f1ba9d9adeedeef5b99b02ba2b0698f8"
+
+[[package]]
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+
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+[[package]]
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+[[package]]
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+name = "windows_x86_64_msvc"
+version = "0.42.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
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+
+[[package]]
+name = "windows_x86_64_msvc"
+version = "0.48.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
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+
 [[package]]
 name = "zeroize"
 version = "1.6.0"
diff --git a/Cargo.toml b/Cargo.toml
index f60ba9d..fa6cc1b 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -35,6 +35,7 @@ sha2 = { version = "0.10.6", optional = true, default-features = false, features
 [dev-dependencies]
 base64ct = { version = "1", features = ["alloc"] }
 hex-literal = "0.4.1"
+proptest = "1"
 serde_test = "1.0.89"
 rand_xorshift = "0.3"
 rand_chacha = "0.3"
diff --git a/tests/proptests.rs b/tests/proptests.rs
new file mode 100644
index 0000000..eaeeebe
--- /dev/null
+++ b/tests/proptests.rs
@@ -0,0 +1,42 @@
+//! Property-based tests.
+
+use proptest::prelude::*;
+use rand_chacha::ChaCha8Rng;
+use rand_core::SeedableRng;
+use rsa::{
+    pkcs1v15,
+    signature::{Keypair, SignatureEncoding, Signer, Verifier},
+    RsaPrivateKey,
+};
+use sha2::Sha256;
+
+prop_compose! {
+    // WARNING: do *NOT* copy and paste this code. It's insecure and optimized for test speed.
+    fn private_key()(seed in any::<[u8; 32]>()) -> RsaPrivateKey {
+        let mut rng = ChaCha8Rng::from_seed(seed);
+        RsaPrivateKey::new(&mut rng, 512).unwrap()
+    }
+}
+
+proptest! {
+    #[test]
+    fn pkcs1v15_sign_roundtrip(private_key in private_key(), msg in any::<Vec<u8>>()) {
+        let signing_key = pkcs1v15::SigningKey::<Sha256>::new(private_key);
+        let signature_bytes = signing_key.sign(&msg).to_bytes();
+
+        let verifying_key = signing_key.verifying_key();
+        let signature = pkcs1v15::Signature::try_from(&*signature_bytes).unwrap();
+        prop_assert!(verifying_key.verify(&msg, &signature).is_ok());
+    }
+
+    // TODO(tarcieri): debug why these are failing
+    // #[test]
+    // fn pss_sign_roundtrip(private_key in private_key(), msg in any::<Vec<u8>>()) {
+    //     let signing_key = pss::SigningKey::<Sha256>::new(private_key);
+    //     let signature_bytes = signing_key.sign(&msg).to_bytes();
+    //
+    //     let verifying_key = signing_key.verifying_key();
+    //     let signature = pss::Signature::try_from(&*signature_bytes).unwrap();
+    //     prop_assert!(verifying_key.verify(&msg, &signature).is_ok());
+    // }
+}