Encrypting second time will give error. Remove .crypt file and it will work again.
crypto-test$ crypto cat.jpg
Please enter your passphrase:
Please enter your passphrase again:
cat.jpg.crypt was generated from cat.jpg
crypto-test$ crypto cat.jpg
Please enter your passphrase:
Please enter your passphrase again:
There was a problem with the execution of gpg. Encryption failed. Error: [can't concat bytes to str]
crypto-test$ rm cat.jpg.crypt
crypto-test$ crypto cat.jpg
Please enter your passphrase:
Please enter your passphrase again:
cat.jpg.crypt was generated from cat.jpg
Mac OS X 10.7.5
gpg (GnuPG) 2.0.27
libgcrypt 1.6.3
crypto 1.4.1
Python 3.4.3
Encrypting second time will give error. Remove .crypt file and it will work again.
Mac OS X 10.7.5 gpg (GnuPG) 2.0.27 libgcrypt 1.6.3 crypto 1.4.1 Python 3.4.3