OSX certtool is a completely different beast from OpenSSL's certtool, 
therefore you see the error
message:

usage:
   Create a keypair and cert: certtool c [options]

....


On Thursday, 20 February 2014 05:23:46 UTC, Kevin Wheelock wrote:
>
> Hi all,
>
> I compiled 6.1.1 on OSX Lion. The compile went flawlessly. I did
>
> ./sage -i openssl
> make ssl
>
> My goal is to run a Sage server. I issued the command
>
> sage: notebook(interface='', ulimit='-v 
> 500000',accounts=True,automatic_login=False, secure=True)
>
> notebook().setup ran automatically. It successfully created cert.cfg and 
> private.pem, but did not create public.pem. And that (eventually) caused the 
> server to fail:
>
> Failed to load application: [Errno 2] No such file or directory: 
> '/Users/wheelock/.sage/notebook/public.pem'
>
> I can run the server in unsecured mode, works great. 
>
> Can anyone shed any light on this? Any tests I could run, or perhaps a fix?
>
> The complete transcript is pasted below.
>
> Thanks much in advance!
>
> Cheers,
>
> K.
>
> ----------------------------------------------------------------
> sage: sage: notebook(interface='', ulimit='-v 
> 500000',accounts=True,automatic_login=False, secure=True)
> The notebook files are stored in: sage_notebook.sagenb
> In order to use an SECURE encrypted notebook, you must first run 
> notebook.setup().
> Now running notebook.setup()
> Domain name [localhost]: kwheelock.info
> Using openssl to generate key
> openssl genrsa 1024 > /Users/wheelock/.sage/notebook/private.pem
> WARNING: can't open config file: 
> /Users/wheelock/Apps/sage-6.1.1/local/openssl/openssl.cnf
> Generating RSA private key, 1024 bit long modulus
> ..++++++
> ....................++++++
> e is 65537 (0x10001)
> certtool --generate-self-signed --template 
> /Users/wheelock/.sage/notebook/cert.cfg --load-privkey 
> /Users/wheelock/.sage/notebook/private.pem --outfile 
> /Users/wheelock/.sage/notebook/public.pem
> usage:
>    Create a keypair and cert: certtool c [options]
>    Create a CSR:              certtool r outFileName [options]
>    Verify a CSR:              certtool v infileName [options]
>    Create a system Identity:  certtool C domainName [options]
>    Import a certificate:      certtool i inFileName [options]
>    Display a certificate:     certtool d inFileName [options]
>    Import a CRL:              certtool I inFileName [options]
>    Display a CRL:             certtool D inFileName [options]
>    Display certs and CRLs in keychain: certtool y [options]
> Options:
>    k=keychainName
>    c (create the keychain)
>    p=passphrase (specify passphrase at keychain creation)
>    o=outFileName (create cert command only)
>    v (verbose)
>    d (infile/outfile in DER format; default is PEM)
>    r=privateKeyFileName (optional; for Import Certificate only)
>    f=[18fo] (private key format = PKCS1/PKCS8/FIPS186; default is PKCS1
>      (openssl) for RSA, openssl for DSA, PKCS8 for Diffie-Hellman,
>      OpenSSL for ECDSA
>    x=[asSm] (Extended Key Usage: a=Any; s=SSL Client; S=SSL Server; m=SMIME)
>    a (create key with default ACL)
>    u (create key with ACL limiting access to current UID)
>    P (Don't create system identity if one already exists for specified domain)
>    h(elp)
> Successfully configured notebook.
> Failed to setup notebook.  Please try notebook.setup() again manually.
> ┌──────────────────────────────────────────────────┐
> │                                                  │
> │ Open your web browser to https://localhost:8080  │
> │                                                  │
> └──────────────────────────────────────────────────┘
> There is an admin account.  If you do not remember the password,
> quit the notebook and type notebook(reset=True).
> Executing twistd  --pidfile="sage_notebook.sagenb/sagenb.pid" -ny 
> "sage_notebook.sagenb/twistedconf.tac"
> /Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Crypto/Util/number.py:57:
>  PowmInsecureWarning: Not using mpz_powm_sec.  You should rebuild using 
> libgmp >= 5 to avoid timing attack vulnerability.
>   _warn("Not using mpz_powm_sec.  You should rebuild using libgmp >= 5 to 
> avoid timing attack vulnerability.", PowmInsecureWarning)
> Unhandled Error
> Traceback (most recent call last):
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/application/app.py",
>  line 642, in run
>     runApp(config)
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/scripts/twistd.py",
>  line 23, in runApp
>     _SomeApplicationRunner(config).run()
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/application/app.py",
>  line 376, in run
>     self.application = self.createOrGetApplication()
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/application/app.py",
>  line 441, in createOrGetApplication
>     application = getApplication(self.config, passphrase)
> --- <exception caught here> ---
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/application/app.py",
>  line 452, in getApplication
>     application = service.loadApplication(filename, style, passphrase)
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/application/service.py",
>  line 405, in loadApplication
>     application = sob.loadValueFromFile(filename, 'application', passphrase)
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/persisted/sob.py",
>  line 210, in loadValueFromFile
>     exec fileObj in d, d
>   File "sage_notebook.sagenb/twistedconf.tac", line 80, in <module>
>     s = 
> strports.service('ssl:8080:interface=:privateKey=/Users/wheelock/.sage/notebook/private.pem:certKey=/Users/wheelock/.sage/notebook/public.pem',
>  site)
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/application/strports.py",
>  line 77, in service
>     endpoints._serverFromStringLegacy(reactor, description, default),
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/internet/endpoints.py",
>  line 1393, in _serverFromStringLegacy
>     nameOrPlugin, args, kw = _parseServer(description, None, default)
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/internet/endpoints.py",
>  line 1384, in _parseServer
>     return (endpointType.upper(),) + parser(factory, *args[1:], **kw)
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/internet/endpoints.py",
>  line 1107, in _parseSSL
>     certPEM = FilePath(certKey).getContent()
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/python/filepath.py",
>  line 287, in getContent
>     fp = self.open()
>   File 
> "/Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/Twisted-13.2.0-py2.7-macosx-10.7-x86_64.egg/twisted/python/filepath.py",
>  line 828, in open
>     return open(self.path, mode + 'b')
> exceptions.IOError: [Errno 2] No such file or directory: 
> '/Users/wheelock/.sage/notebook/public.pem'
>
> Failed to load application: [Errno 2] No such file or directory: 
> '/Users/wheelock/.sage/notebook/public.pem'
>
> ---------------------------------------------------------------------------
> error                                     Traceback (most recent call last)
> <ipython-input-1-37a87ab79ab1> in <module>()
> ----> 1 notebook(interface='', ulimit='-v 
> 500000',accounts=True,automatic_login=False, secure=True)
>
> /Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/sage/misc/lazy_import.so
>  in sage.misc.lazy_import.LazyImport.__call__ (sage/misc/lazy_import.c:2550)()
>
> /Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/sagenb-0.10.8.2-py2.7.egg/sagenb/notebook/notebook_object.py
>  in __call__(self, *args, **kwds)
>     226     """
>     227     def __call__(self, *args, **kwds):
> --> 228         return self.notebook(*args, **kwds)
>     229 
>     230     notebook = run_notebook.notebook_run
>
> /Users/wheelock/Apps/sage/local/lib/python2.7/site-packages/sagenb-0.10.8.2-py2.7.egg/sagenb/notebook/run_notebook.py
>  in notebook_run(self, directory, port, interface, port_tries, secure, reset, 
> accounts, openid, server_pool, ulimit, timeout, doc_timeout, upload, 
> automatic_login, start_path, fork, quiet, server, profile, subnets, 
> require_login, open_viewer, address)
>     630     os.chdir(cwd)
>     631     if e == 256:
> --> 632         raise socket.error
>     633 
>     634 def get_admin_passwd():
>
> error:
> ----------------------------------------------------------------
>
>
>

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