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Unhandled exception: Invalid EVP_PKEY: error:0D0680A8:asn1 encoding routines:ASN1_CHECK_TLEN:wrong tag (OpenSSL::PKey::PKeyError)
  from lib/openssl_ext/src/openssl_ext/pkey.cr:9:7 in 'initialize'
  from lib/openssl_ext/src/openssl_ext/pkey.cr:8:5 in 'new'
  from lib/openssl_ext/src/openssl_ext/pkey.cr:28:11 in 'new'
  from lib/openssl_ext/src/openssl_ext/pkey.cr:18:7 in 'new'
  from lib/openssl_ext/src/openssl_ext/pkey.cr:16:5 in 'new'
  from lib/jwt/src/jwt.cr:102:34 in 'sign'
  from lib/jwt/src/jwt.cr:88:17 in 'encoded_signature'
  from lib/jwt/src/jwt.cr:25:5 in 'encode'
  from src/google-jwt-test.cr:13:5 in 'run'
  from src/google-jwt-test.cr:31:1 in '__crystal_main'
  from /usr/local/Cellar/crystal/0.29.0/src/crystal/main.cr:97:5 in 'main_user_code'
  from /usr/local/Cellar/crystal/0.29.0/src/crystal/main.cr:86:7 in 'main'
  from /usr/local/Cellar/crystal/0.29.0/src/crystal/main.cr:106:3 in 'main'

Crystal 0.29.0 (2019-06-06)

LLVM: 6.0.1
Default target: x86_64-apple-macosx

rishav@rishav-sbook:~/digglu$ shards update
Resolving dependencies
Fetching https://github.com/will/crystal-pg.git
Fetching https://github.com/gdotdesign/cr-dotenv.git
Fetching https://github.com/crystal-community/jwt.git
Fetching https://github.com/evanhahn/crystal-helmet.git
Fetching https://github.com/crystal-lang/crystal-db.git
Fetching https://github.com/spider-gazelle/openssl_ext.git
Unable to satisfy the following requirements:

- `crystal (>= 0.35.0, < 2.0.0)` required by `pg 0.23.2`
- `crystal (>= 0.34.0, < 2.0.0)` required by `dotenv 1.0.0`
- `crystal (>= 0.36.1)` required by `jwt 1.5.1`
- `crystal (< 1.0.0)` required by `helmet 0.2.2`
- `crystal (>= 0.35.0, < 2.0.0)` required by `db 0.10.1`
- `crystal (>= 0.36.1)` required by `openssl_ext 2.1.4`
Failed to resolve dependencies, try updating incompatible shards or use --ignore-crystal-version as a workaround if no update is available.

...
Installing jwt (0.1.0 at 0.2.2)
...

aaron@t430:~/Documents/ogreets/OGV3/lib/jwt$ shards install
Fetching https://github.com/stakach/openssl_ext.git
Installing openssl_ext (1.0.0)
aaron@t430:~/Documents/ogreets/OGV3/lib/jwt$ crystal run examples/basic_usage.cr 
In src/jwt.cr:116:29

 116 | if exp.to_s.to_i < Time.now.to_unix
                               ^--
Warning: Deprecated Time.now. Use `Time.local` or `Time.utc` instead.

In src/jwt.cr:122:29

 122 | if nbf.to_s.to_i > Time.now.to_unix
                               ^--
Warning: Deprecated Time.now. Use `Time.local` or `Time.utc` instead.

A total of 2 warnings were found.
"eyJ0eXAiOiJKV1QiLCJhbGciOiJIUzI1NiJ9.eyJmb28iOiJiYXIifQ.Y3shN5Wh4FmOPM34biIm9QQmat373hJFKNxgSANQWJo"
{"foo" => "bar"}
{"typ" => "JWT", "alg" => "HS256"}
aaron@t430:~/Documents/ogreets/OGV3/lib/jwt$ 

17 | token = JWT.encode(uh, "secretpass", JWT::Algorithm::HS256)
                  ^-----
Error: instantiating 'JWT:Module#encode(Hash(String, Bool | Int32 | String | Nil), String, JWT::Algorithm)'


In lib/jwt/src/jwt.cr:25:17

 25 | segments << encoded_signature(algorithm, key, segments.join("."))
                  ^----------------
Error: instantiating 'encoded_signature(JWT::Algorithm, String, String)'


In lib/jwt/src/jwt.cr:88:17

 88 | signature = sign(algorithm, key, data)
                  ^---
Error: instantiating 'sign(JWT::Algorithm, String, String)'


In lib/jwt/src/jwt.cr:102:20

 102 | OpenSSL::RSA.new(key).sign(OpenSSL::Digest.new("sha256"), data)
                    ^--
Error: instantiating 'OpenSSL::RSA.class#new(String)'


In lib/openssl_ext/src/openssl_ext/pkey.cr:16:5

 16 | def self.new(encoded : String, passphrase = nil, is_private = true)
      ^--
Error: instantiating 'new(String, Nil, Bool)'


In lib/openssl_ext/src/openssl_ext/pkey.cr:18:12

 18 | self.new(IO::Memory.new(encoded), passphrase, is_private)
           ^--
Error: instantiating 'OpenSSL::RSA.class#new(IO::Memory, Nil, Bool)'


In lib/openssl_ext/src/openssl_ext/pkey.cr:24:26

 24 | bio = GETS_BIO.new(io)
                     ^--
Error: instantiating 'OpenSSL::GETS_BIO.class#new(IO::Memory)'


In lib/openssl_ext/src/openssl_ext/bio.cr:16:10

 16 | io.seek(position)
         ^---
Error: instantiating 'IO+#seek((Int32 | Int64))'

==29088== 316,624 (215,880 direct, 100,744 indirect) bytes in 1,799 blocks are definitely lost in loss record 110 of 110
==29088==    at 0x4C2FB0F: malloc (in /usr/lib/valgrind/vgpreload_memcheck-amd64-linux.so)
==29088==    by 0x5243F08: CRYPTO_zalloc (in /usr/lib/x86_64-linux-gnu/libcrypto.so.1.1)
==29088==    by 0x517513C: BIO_new (in /usr/lib/x86_64-linux-gnu/libcrypto.so.1.1)
==29088==    by 0x2362D6: *OpenSSL::GETS_BIO#initialize<IO::Memory>:Nil (bio.cr:37)
==29088==    by 0x236296: *OpenSSL::GETS_BIO::new<IO::Memory>:OpenSSL::GETS_BIO (bio.cr:36)
==29088==    by 0x235D23: *OpenSSL::PKey::RSA::new<IO::Memory, Nil>:OpenSSL::PKey::RSA (rsa.cr:20)
==29088==    by 0x235C5D: *OpenSSL::PKey::RSA::new<String, Nil>:OpenSSL::PKey::RSA (rsa.cr:10)
==29088==    by 0x235C42: *OpenSSL::PKey::RSA::new<String>:OpenSSL::PKey::RSA (rsa.cr:9)
==29088==    by 0x16B515: __crystal_main (my_test.cr:18)

loop do
  rsa = OpenSSL::PKey::RSA.new(MY_KEY_HERE)
end

$ crystal test.cr
JWT.decode(token, "hello, there", JWT::Algorithm::HS256) # => Unhandled exception: cast from String to Hash(K, V) failed, at /usr/lib/crystal/json/any.cr:239:5:239 (TypeCastError)
  from /usr/lib/crystal/json/any.cr:239:5 in 'as_h'
  from lib/jwt/src/jwt.cr:72:15 in 'decode'
  from broken?.cr:6:5 in '__crystal_main'
  from /usr/lib/crystal/crystal/main.cr:97:5 in 'main_user_code'
  from /usr/lib/crystal/crystal/main.cr:86:7 in 'main'
  from /usr/lib/crystal/crystal/main.cr:106:3 in 'main'
  from __libc_start_main
  from _start
  from ???
$ 

$ Crystal 0.32.0 (2019-12-12)

LLVM: 9.0.0
Default target: x86_64-pc-linux-gnu