Manually depad RSAES-PKCS1 on Apple OSes

src/libraries/Common/src/Interop/OSX/System.Security.Cryptography.Native.Apple/Interop.RSA.cs

@@ -2,6 +2,7 @@
 // The .NET Foundation licenses this file to you under the MIT license.
 
 using System;
+using System.Buffers;
 using System.Diagnostics;
 using System.Runtime.InteropServices;
 using System.Security.Cryptography;
@@ -69,8 +70,8 @@ private static partial int RsaDecryptOaep(
             out SafeCFDataHandle pEncryptedOut,
             out SafeCFErrorHandle pErrorOut);
 
-        [LibraryImport(Libraries.AppleCryptoNative, EntryPoint = "AppleCryptoNative_RsaDecryptPkcs")]
-        private static partial int RsaDecryptPkcs(
+        [LibraryImport(Libraries.AppleCryptoNative, EntryPoint = "AppleCryptoNative_RsaDecryptRaw")]
+        private static partial int RsaDecryptRaw(
             SafeSecKeyRefHandle publicKey,
             ReadOnlySpan<byte> pbData,
             int cbData,
@@ -166,17 +167,40 @@ internal static byte[] RsaDecrypt(
             byte[] data,
             RSAEncryptionPadding padding)
         {
+            if (padding == RSAEncryptionPadding.Pkcs1)
+            {
+                byte[] padded = ExecuteTransform(
+                    data,
+                    (ReadOnlySpan<byte> source, out SafeCFDataHandle decrypted, out SafeCFErrorHandle error) =>
+                        RsaDecryptRaw(privateKey, source, source.Length, out decrypted, out error));
+
+                byte[] depad = CryptoPool.Rent(padded.Length);
+                OperationStatus status = RsaPaddingProcessor.DepadPkcs1Encryption(padded, depad, out int written);
+                byte[]? ret = null;
+
+                if (status == OperationStatus.Done)
+                {
+                    ret = depad.AsSpan(0, written).ToArray();
+                }
+
+                // Clear the whole thing, especially on failure.
+                CryptoPool.Return(depad);
+                CryptographicOperations.ZeroMemory(padded);
+
+                if (ret is null)
+                {
+                    throw new CryptographicException(SR.Cryptography_InvalidPadding);
+                }
+
+                return ret;
+            }
+
+            Debug.Assert(padding.Mode == RSAEncryptionPaddingMode.Oaep);
+
             return ExecuteTransform(
                 data,
                 (ReadOnlySpan<byte> source, out SafeCFDataHandle decrypted, out SafeCFErrorHandle error) =>
                 {
-                    if (padding == RSAEncryptionPadding.Pkcs1)
-                    {
-                        return RsaDecryptPkcs(privateKey, source, source.Length, out decrypted, out error);
-                    }
-
-                    Debug.Assert(padding.Mode == RSAEncryptionPaddingMode.Oaep);
-
                     return RsaDecryptOaep(
                         privateKey,
                         source,
@@ -195,14 +219,63 @@ internal static bool TryRsaDecrypt(
             out int bytesWritten)
         {
             Debug.Assert(padding.Mode == RSAEncryptionPaddingMode.Pkcs1 || padding.Mode == RSAEncryptionPaddingMode.Oaep);
+
+            if (padding.Mode == RSAEncryptionPaddingMode.Pkcs1)
+            {
+                byte[] padded = CryptoPool.Rent(source.Length);
+                byte[] depad = CryptoPool.Rent(source.Length);
+
+                bool processed = TryExecuteTransform(
+                    source,
+                    padded,
+                    out int paddedLength,
+                    (ReadOnlySpan<byte> innerSource, out SafeCFDataHandle outputHandle, out SafeCFErrorHandle errorHandle) =>
+                        RsaDecryptRaw(privateKey, innerSource, innerSource.Length, out outputHandle, out errorHandle));
+
+                Debug.Assert(
+                    processed,
+                    "TryExecuteTransform should always return true for a large enough buffer.");
+
+                OperationStatus status = OperationStatus.InvalidData;
+                int depaddedLength = 0;
+
+                if (processed)
+                {
+                    status = RsaPaddingProcessor.DepadPkcs1Encryption(
+                        new ReadOnlySpan<byte>(padded, 0, paddedLength),
+                        depad,
+                        out depaddedLength);
+                }
+
+                CryptoPool.Return(padded);
+
+                if (status == OperationStatus.Done)
+                {
+                    if (depaddedLength <= destination.Length)
+                    {
+                        depad.AsSpan(0, depaddedLength).CopyTo(destination);
+                        CryptoPool.Return(depad);
+                        bytesWritten = depaddedLength;
+                        return true;
+                    }
+
+                    CryptoPool.Return(depad);
+                    bytesWritten = 0;
+                    return false;
+                }
+
+                CryptoPool.Return(depad);
+                Debug.Assert(status == OperationStatus.InvalidData);
+                throw new CryptographicException(SR.Cryptography_InvalidPadding);
+            }
+
             return TryExecuteTransform(
                 source,
                 destination,
                 out bytesWritten,
                 delegate (ReadOnlySpan<byte> innerSource, out SafeCFDataHandle outputHandle, out SafeCFErrorHandle errorHandle)
                 {
-                    return padding.Mode == RSAEncryptionPaddingMode.Pkcs1 ?
-                        RsaDecryptPkcs(privateKey, innerSource, innerSource.Length, out outputHandle, out errorHandle) :
+                    return
                         RsaDecryptOaep(privateKey, innerSource, innerSource.Length, PalAlgorithmFromAlgorithmName(padding.OaepHashAlgorithm), out outputHandle, out errorHandle);
                 });
         }

src/libraries/Common/src/System/Security/Cryptography/RsaPaddingProcessor.cs

@@ -1,6 +1,7 @@
 // Licensed to the .NET Foundation under one or more agreements.
 // The .NET Foundation licenses this file to you under the MIT license.
 
+using System.Buffers;
 using System.Buffers.Binary;
 using System.Collections.Concurrent;
 using System.Diagnostics;
@@ -142,6 +143,109 @@ internal static void PadPkcs1Encryption(
             source.CopyTo(mInEM);
         }
 
+        internal static OperationStatus DepadPkcs1Encryption(
+            ReadOnlySpan<byte> source,
+            Span<byte> destination,
+            out int bytesWritten)
+        {
+            int primitive = DepadPkcs1Encryption(source);
+            int primitiveSign = SignStretch(primitive);
+
+            // Primitive is a positive length, or ~length to indicate
+            // an error, so flip ~length to length if the high bit is set.
+            int len = Choose(primitiveSign, ~primitive, primitive);
+            int spaceRemain = destination.Length - len;
+            int spaceRemainSign = SignStretch(spaceRemain);
+
+            // len = clampHigh(len, destination.Length);
+            len = Choose(spaceRemainSign, destination.Length, len);
+
+            // ret = spaceRemain < 0 ? DestinationTooSmall : Done
+            int ret = Choose(
+                spaceRemainSign,
+                (int)OperationStatus.DestinationTooSmall,
+                (int)OperationStatus.Done);
+
+            // ret = primitive < 0 ? InvalidData : ret;
+            ret = Choose(primitiveSign, (int)OperationStatus.InvalidData, ret);
+
+            // Write some number of bytes, regardless of the final return.
+            source[^len..].CopyTo(destination);
+
+            // bytesWritten = ret == Done ? len : 0;
+            bytesWritten = Choose(CheckZero(ret), len, 0);
+            return (OperationStatus)ret;
+        }
+
+        private static int DepadPkcs1Encryption(ReadOnlySpan<byte> source)
+        {
+            Debug.Assert(source.Length > 11);
+            ReadOnlySpan<byte> afterPadding = source.Slice(10);
+            ReadOnlySpan<byte> noZeros = source.Slice(2, 8);
+
+            // Find the first zero in noZeros, or -1 for no zeros.
+            int zeroPos = BlindFindFirstZero(noZeros);
+
+            // If zeroPos is negative, valid is -1, otherwise 0.
+            int valid = SignStretch(zeroPos);
+
+            // If there are no zeros in afterPadding then zeroPos is negative,
+            // so negating the sign stretch is 0, which makes hasPos 0.
+            // If there -was- a zero, sign stretching is 0, so negating it makes hasPos -1.
+            zeroPos = BlindFindFirstZero(afterPadding);
+            int hasLen = ~SignStretch(zeroPos);
+            valid &= hasLen;
+
+            // Check that the first two bytes are { 00 02 }
+            valid &= CheckZero(source[0] | (source[1] ^ 0x02));
+
+            int lenIfGood = afterPadding.Length - zeroPos - 1;
+            // If there were no zeros, use the full after-min-padding segment.
+            int lenIfBad = ~Choose(hasLen, lenIfGood, source.Length - 11);
+
+            Debug.Assert(lenIfBad < 0);
+            return Choose(valid, lenIfGood, lenIfBad);
+        }
+
+        private static int BlindFindFirstZero(ReadOnlySpan<byte> source)
+        {
+            // Any vectorization of this routine needs to use non-early termination,
+            // and instructions that do not vary their completion time on the input.
+
+            int pos = -1;
+
+            for (int i = source.Length - 1; i >= 0; i--)
+            {
+                // pos = source[i] == 0 ? i : pos;
+                int local = CheckZero(source[i]);
+                pos = Choose(local, i, pos);
+            }
+
+            return pos;
+        }
+
+        private static int SignStretch(int value)
+        {
+            return value >> 31;
+        }
+
+        private static int Choose(int selector, int yes, int no)
+        {
+            Debug.Assert((selector | (selector - 1)) == -1);
+            return (selector & yes) | (~selector & no);
+        }
+
+        private static int CheckZero(int value)
+        {
+            // For zero, ~value and value-1 are both all bits set (negative).
+            // For positive values, ~value is negative and value-1 is positive.
+            // For negative values except MinValue, ~value is positive and value-1 is negative.
+            // For MinValue, ~value is positive and value-1 is also positive.
+            // All together, the only thing that has negative & negative is 0, so stretch the sign bit.
+            int mask = ~value & (value - 1);
+            return SignStretch(mask);
+        }
+
         internal static void PadPkcs1Signature(
             HashAlgorithmName hashAlgorithmName,
             ReadOnlySpan<byte> source,

src/libraries/Common/tests/System/Security/Cryptography/AlgorithmImplementations/RSA/EncryptDecrypt.cs

@@ -2,6 +2,8 @@
 // The .NET Foundation licenses this file to you under the MIT license.
 
 using System.Collections.Generic;
+using System.Diagnostics;
+using System.Numerics;
 using Test.Cryptography;
 using Microsoft.DotNet.XUnitExtensions;
 using Xunit;
@@ -736,6 +738,119 @@ public void Decrypt_Pkcs1_ErrorsForInvalidPadding(byte[] data)
             }
         }
 
+        [Fact]
+        public void Decrypt_Pkcs1_BadPadding()
+        {
+            if ((PlatformDetection.IsWindows && !PlatformDetection.IsWindows10Version2004OrGreater))
+            {
+                return;
+            }
+
+            RSAParameters keyParams = TestData.RSA2048Params;
+            BigInteger e = new BigInteger(keyParams.Exponent, true, true);
+            BigInteger n = new BigInteger(keyParams.Modulus, true, true);
+            byte[] buf = new byte[keyParams.Modulus.Length];
+            byte[] c = new byte[buf.Length];
+
+            buf[1] = 2;
+            buf.AsSpan(2).Fill(1);
+
+            ref byte afterMinPadding = ref buf[10];
+            ref byte lastByte = ref buf[^1];
+            afterMinPadding = 0;
+
+            using (RSA rsa = RSAFactory.Create(keyParams))
+            {
+                RawEncrypt(buf, e, n, c);
+                // Assert.NoThrow, check that manual padding is coherent
+                Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1);
+
+                // All RSA encryption schemes start with 00, so pick any other number.
+                //
+                // If buf > modulus then encrypt should fail, so this
+                // is the largest legal-but-invalid value to test.
+                buf[0] = keyParams.Modulus[0];
+                RawEncrypt(buf, e, n, c);
+                Assert.ThrowsAny<CryptographicException>(() => Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1));
+
+                // Check again with a zero length payload
+                (afterMinPadding, lastByte) = (lastByte, afterMinPadding);
+                RawEncrypt(buf, e, n, c);
+                Assert.ThrowsAny<CryptographicException>(() => Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1));
+
+                // Back to valid padding
+                buf[0] = 0;
+                (afterMinPadding, lastByte) = (lastByte, afterMinPadding);
+                RawEncrypt(buf, e, n, c);
+                Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1);
+
+                // This is (sort of) legal for PKCS1 signatures, but not decryption.
+                buf[1] = 1;
+                RawEncrypt(buf, e, n, c);
+                Assert.ThrowsAny<CryptographicException>(() => Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1));
+
+                // No RSA PKCS1 padding scheme starts with 00 FF.
+                buf[1] = 255;
+                RawEncrypt(buf, e, n, c);
+                Assert.ThrowsAny<CryptographicException>(() => Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1));
+
+                // Check again with a zero length payload
+                (afterMinPadding, lastByte) = (lastByte, afterMinPadding);
+                RawEncrypt(buf, e, n, c);
+                Assert.ThrowsAny<CryptographicException>(() => Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1));
+
+                // Back to valid padding
+                buf[1] = 2;
+                (afterMinPadding, lastByte) = (lastByte, afterMinPadding);
+                RawEncrypt(buf, e, n, c);
+                Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1);
+
+                // Try a zero in every possible required padding position
+                for (int i = 2; i < 10; i++)
+                {
+                    buf[i] = 0;
+
+                    RawEncrypt(buf, e, n, c);
+                    Assert.ThrowsAny<CryptographicException>(() => Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1));
+
+                    // It used to be 1, now it's 2, still not zero.
+                    buf[i] = 2;
+                }
+
+                // Back to valid padding
+                RawEncrypt(buf, e, n, c);
+                Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1);
+
+                // Make it such that
+                // "there is no octet with hexadecimal value 0x00 to separate PS from M"
+                // (RFC 3447 sec 7.2.2, rule 3, third clause)
+                buf.AsSpan(10).Fill(3);
+                RawEncrypt(buf, e, n, c);
+                Assert.ThrowsAny<CryptographicException>(() => Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1));
+
+                // Every possible problem, for good measure.
+                buf[0] = 2;
+                buf[1] = 0;
+                buf[4] = 0;
+                RawEncrypt(buf, e, n, c);
+                Assert.ThrowsAny<CryptographicException>(() => Decrypt(rsa, c, RSAEncryptionPadding.Pkcs1));
+            }
+
+            static void RawEncrypt(ReadOnlySpan<byte> source, BigInteger e, BigInteger n, Span<byte> destination)
+            {
+                BigInteger m = new BigInteger(source, true, true);
+                BigInteger c = BigInteger.ModPow(m, e, n);
+                int shift = destination.Length - c.GetByteCount(true);
+                destination.Slice(0, shift).Clear();
+                bool wrote = c.TryWriteBytes(destination.Slice(shift), out int written, true, true);
+
+                if (!wrote || written + shift != destination.Length)
+                {
+                    throw new UnreachableException();
+                }
+            }
+        }
+
         public static IEnumerable<object[]> OaepPaddingModes
         {
             get

src/native/libs/System.Security.Cryptography.Native.Apple/entrypoints.c

@@ -70,6 +70,7 @@ static const Entry s_cryptoAppleNative[] =
     DllImportEntry(AppleCryptoNative_RsaGenerateKey)
     DllImportEntry(AppleCryptoNative_RsaDecryptOaep)
     DllImportEntry(AppleCryptoNative_RsaDecryptPkcs)
+    DllImportEntry(AppleCryptoNative_RsaDecryptRaw)
     DllImportEntry(AppleCryptoNative_RsaEncryptOaep)
     DllImportEntry(AppleCryptoNative_RsaEncryptPkcs)
     DllImportEntry(AppleCryptoNative_RsaSignaturePrimitive)