Add local TLS server

This also adds certificates for testing purposes and files to make it
easy to generate/regenerate them.

This also replaces an existing test of how we utilize our pool manager
such that we don't connect to badssl.com

Finally, this adds additional context parameters for our pool manager to
account for mTLS certificates used by clients to authenticate to a
server.

ROADMAP.rst

@@ -0,0 +1,6 @@
+- Environment Manager - with caching
+
+- SSL Context Factory + Plumbing through to urllib3
+
+- Can we make Transport Adapters composable? Should we abandon that idea and
+  instead make a collaborator object that's composable?

src/requests/adapters.py

@@ -73,7 +73,9 @@ def SOCKSProxyManager(*args, **kwargs):
 
 
 def _urllib3_request_context(
-    request: "PreparedRequest", verify: "bool | str | None"
+    request: "PreparedRequest",
+    verify: "bool | str | None",
+    client_cert: "typing.Tuple[str, str] | str | None",
 ) -> "(typing.Dict[str, typing.Any], typing.Dict[str, typing.Any])":
     host_params = {}
     pool_kwargs = {}
@@ -86,6 +88,14 @@ def _urllib3_request_context(
     if isinstance(verify, str):
         pool_kwargs["ca_certs"] = verify
     pool_kwargs["cert_reqs"] = cert_reqs
+    if client_cert is not None:
+        if isinstance(client_cert, tuple) and len(client_cert) == 2:
+            pool_kwargs["cert_file"] = client_cert[0]
+            pool_kwargs["key_file"] = client_cert[1]
+        else:
+            # According to our docs, we allow users to specify just the client
+            # cert path
+            pool_kwargs["cert_file"] = client_cert
     host_params = {
         "scheme": scheme,
         "host": parsed_request_url.hostname,
@@ -354,13 +364,13 @@ def build_response(self, req, resp):
 
         return response
 
-    def _get_connection(self, request, verify, proxies=None):
+    def _get_connection(self, request, verify, proxies=None, cert=None):
         # Replace the existing get_connection without breaking things and
         # ensure that TLS settings are considered when we interact with
         # urllib3 HTTP Pools
         proxy = select_proxy(request.url, proxies)
         try:
-            host_params, pool_kwargs = _urllib3_request_context(request, verify)
+            host_params, pool_kwargs = _urllib3_request_context(request, verify, cert)
         except ValueError as e:
             raise InvalidURL(e, request=request)
         if proxy:
@@ -509,7 +519,7 @@ def send(
         """
 
         try:
-            conn = self._get_connection(request, verify, proxies)
+            conn = self._get_connection(request, verify, proxies=proxies, cert=cert)
         except LocationValueError as e:
             raise InvalidURL(e, request=request)
 

tests/certs/README.md

@@ -0,0 +1,10 @@
+# Testing Certificates
+
+This is a collection of certificates useful for testing aspects of Requests'
+behaviour.
+
+The certificates include:
+
+* [expired](./expired) server certificate with a valid certificate authority
+* [mtls](./mtls) provides a valid client certificate with a 2 year validity
+* [valid](./valid) has a valid server certificate

tests/certs/expired/Makefile

@@ -0,0 +1,13 @@
+.PHONY: all clean ca server
+
+ca:
+	make -C $@ all
+
+server:
+	make -C $@ all
+
+all: ca server
+
+clean:
+	make -C ca clean
+	make -C server clean

tests/certs/expired/README.md

@@ -0,0 +1,11 @@
+# Expired Certificates and Configuration for Testing
+
+This has a valid certificate authority in [ca](./ca) and an invalid server
+certificate in [server](./server).
+
+This can all be regenerated with:
+
+```
+make clean
+make all
+```

tests/certs/expired/ca/Makefile

@@ -0,0 +1,13 @@
+.PHONY: all clean
+
+root_files = ca-private.key ca.crt
+
+ca-private.key:
+	openssl genrsa -out ca-private.key 2048
+
+all: ca-private.key
+	openssl req -x509 -sha256 -days 7300 -key ca-private.key -out ca.crt -config ca.cnf
+	ln -s ca.crt cacert.pem
+
+clean:
+	rm -f cacert.pem ca.crt ca-private.key *.csr

tests/certs/expired/ca/ca-private.key

@@ -0,0 +1,28 @@
+-----BEGIN PRIVATE KEY-----
+MIIEvQIBADANBgkqhkiG9w0BAQEFAASCBKcwggSjAgEAAoIBAQDHlIhe7GLCeSk8
+RZOKdtmyKns6KdZgGw/LcxPkYvQlu1g0zV8X0DqVr2LdMumWUTNCc9sPdSlAG+He
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+26qSPQ0/aF9nagb5eHX3AuU=
+-----END PRIVATE KEY-----

tests/certs/expired/ca/ca.cnf

@@ -0,0 +1,12 @@
+[req]
+default_bits = 2048
+prompt = no
+default_md = sha256
+encrypt_key = no
+distinguished_name = dn
+
+[dn]
+C = US                            # country code
+O = Python Software Foundation    # organization
+OU = python-requests              # organization unit/department
+CN = Self-Signed Root CA          # common name / your cert name

tests/certs/expired/ca/ca.crt

@@ -0,0 +1,20 @@
+-----BEGIN CERTIFICATE-----
+MIIDWzCCAkMCFA9wdtNh/V99DRwYp8vXjPxSjJnWMA0GCSqGSIb3DQEBCwUAMGox
+CzAJBgNVBAYTAlVTMSMwIQYDVQQKDBpQeXRob24gU29mdHdhcmUgRm91bmRhdGlv
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+-----END CERTIFICATE-----

tests/certs/expired/ca/ca.srl

@@ -0,0 +1 @@
+4F36C3A7E075BA6452D10EEB81E7F189FF489B74

tests/certs/expired/server/Makefile

@@ -0,0 +1,16 @@
+.PHONY: all clean
+
+server.key:
+	openssl genrsa -out $@ 2048
+
+server.csr: server.key
+	openssl req -key $< -new -out $@ -config cert.cnf
+
+server.pem: server.csr
+	openssl x509 -req -CA ../ca/ca.crt -CAkey ../ca/ca-private.key -in server.csr -outform PEM -out server.pem -days 0 -CAcreateserial
+	openssl x509 -in ../ca/ca.crt -outform PEM >> $@
+
+all: server.pem
+
+clean:
+	rm -f server.*

tests/certs/expired/server/cert.cnf

@@ -0,0 +1,24 @@
+[req]
+req_extensions = v3_req
+distinguished_name = req_distinguished_name
+prompt=no
+
+[req_distinguished_name]
+C = US
+ST = DE
+O = Python Software Foundation
+OU = python-requests
+CN = localhost
+
+[v3_req]
+# Extensions to add to a certificate request
+basicConstraints = CA:FALSE
+keyUsage = digitalSignature, keyEncipherment
+extendedKeyUsage = serverAuth
+subjectAltName = @alt_names
+
+[alt_names]
+DNS.1 = *.localhost
+DNS.1 = localhost
+IP.1 = 127.0.0.1
+IP.2 = ::1

tests/certs/expired/server/server.csr

@@ -0,0 +1,19 @@
+-----BEGIN CERTIFICATE REQUEST-----
+MIIDHjCCAgYCAQAwbTELMAkGA1UEBhMCVVMxCzAJBgNVBAgMAkRFMSMwIQYDVQQK
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+-----END CERTIFICATE REQUEST-----

tests/certs/expired/server/server.key

@@ -0,0 +1,28 @@
+-----BEGIN PRIVATE KEY-----
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+-----END PRIVATE KEY-----

tests/certs/expired/server/server.pem

@@ -0,0 +1,41 @@
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+-----BEGIN CERTIFICATE-----
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+Kt1OLwnZyhfRoSUesoEqpP68vzWEgiYv0QuIWvzNt0YfAAvEgGoc3iri44MelKLn
+9ZMT8m91nVamA35R8ZjfeAkNp2xcz0a67V0ww6o4wSXrG7o5ZRXyjqZ/9K7SfwUJ
+rV9RciccsjH/MzKbfrx73QwsbPWiFmjzHopdasIO0lDlmgm/r9gKfkbzfKoGCgLZ
+6an6FlmLftLSXijf/QwtqeSP9fODeE3dzBmnTM3jdoVS53ZegUDWNl14o25v2Kg=
+-----END CERTIFICATE-----

tests/certs/mtls/Makefile

@@ -0,0 +1,7 @@
+.PHONY: all clean
+
+all:
+	make -C client all
+
+clean:
+	make -C client clean

tests/certs/mtls/README.md

@@ -0,0 +1,4 @@
+# Certificate Examples for mTLS
+
+This has some generated certificates for mTLS utilization. The idea is to be
+able to have testing around how Requests handles client certificates.

tests/certs/mtls/client/Makefile

@@ -0,0 +1,16 @@
+.PHONY: all clean
+
+client.key:
+	openssl genrsa -out $@ 2048
+
+client.csr: client.key
+	openssl req -key $< -new -out $@ -config cert.cnf
+
+client.pem: client.csr
+	openssl x509 -req -CA ./ca/ca.crt -CAkey ./ca/ca-private.key -in client.csr -outform PEM -out client.pem -days 730 -CAcreateserial
+	openssl x509 -in ./ca/ca.crt -outform PEM >> $@
+
+all: client.pem
+
+clean:
+	rm -f client.*

tests/certs/mtls/client/ca

@@ -0,0 +1 @@
+../../expired/ca/

tests/certs/mtls/client/cert.cnf

@@ -0,0 +1,26 @@
+[req]
+req_extensions = v3_req
+distinguished_name = req_distinguished_name
+prompt=no
+
+[req_distinguished_name]
+C = US
+ST = DE
+O = Python Software Foundation
+OU = python-requests
+CN = requests
+
+[v3_req]
+# Extensions to add to a certificate request
+basicConstraints = CA:FALSE
+keyUsage = digitalSignature, keyEncipherment
+extendedKeyUsage = clientAuth
+subjectAltName = @alt_names
+
+[alt_names]
+DNS.1 = *.localhost
+IP.1 = 127.0.0.1
+IP.2 = ::1
+URI.1 = spiffe://trust.python.org/v0/maintainer/sigmavirus24/project/requests/org/psf
+URI.2 = spiffe://trust.python.org/v1/maintainer:sigmavirus24/project:requests/org:psf
+URI.3 = spiffe://trust.python.org/v1/maintainer=sigmavirus24/project=requests/org=psf

tests/certs/mtls/client/client.csr

@@ -0,0 +1,24 @@
+-----BEGIN CERTIFICATE REQUEST-----
+MIIEGjCCAwICAQAwbDELMAkGA1UEBhMCVVMxCzAJBgNVBAgMAkRFMSMwIQYDVQQK
+DBpQeXRob24gU29mdHdhcmUgRm91bmRhdGlvbjEYMBYGA1UECwwPcHl0aG9uLXJl
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+BgEFBQcDAjCCAR8GA1UdEQSCARYwggESggsqLmxvY2FsaG9zdIcEfwAAAYcQAAAA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==
+-----END CERTIFICATE REQUEST-----