MITM Proxy

.gitignore

@@ -8,3 +8,8 @@
 /shard.lock
 
 /http_proxy
+
+# Local MITM certificates/keys generated for manual testing
+/.mitm-certs/
+/mitm-ca.*
+/mitm.*

MITM_CHECKLIST.md

@@ -0,0 +1,65 @@
+# MITM Production Readiness Checklist
+
+Status key:
+
+- [x] Done
+- [ ] Not done
+- [~] Partial
+
+## Security
+
+- [ ] Store CA private key outside repository with strict permissions (`600`) and dedicated service account.
+- [ ] Add CA key rotation procedure and documented migration plan.
+- [ ] Add encrypted CA key / passphrase support.
+- [~] Keep sensitive logging disabled by default (`debug: false`), but add redaction for auth/cookies/tokens when debug is enabled.
+- [ ] Add host allowlist/denylist policy for MITM interception.
+
+## Certificate Generation
+
+- [x] Dynamic per-host certificate generation is implemented.
+- [x] In-process generator is implemented in `src/http/proxy/server/certificate_generator.cr`.
+- [x] Certificate cache directory support exists (`certificate_cache_dir`).
+- [x] Basic SAN generation exists for DNS/IP hostnames.
+- [ ] Serial number strategy should be strengthened (currently timestamp-based).
+- [ ] Add cert cache lifecycle controls (TTL/max size/pruning).
+
+## Protocol Behavior
+
+- [x] CONNECT MITM flow for HTTP/1.1 is implemented.
+- [x] ALPN is constrained to HTTP/1.1 in server contexts.
+- [~] Non-HTTP streams are detected and aborted in MITM path; consider explicit passthrough/tunnel fallback policy.
+- [ ] Define and document policy for HTTP/2/HTTP/3 handling in production mode.
+
+## Reliability & Resilience
+
+- [x] Mutex-protected per-host context cache prevents concurrent generation races.
+- [ ] Add bounded concurrency / connection limits.
+- [ ] Add timeout and retry policy for upstream requests and TLS handshakes.
+- [ ] Add graceful shutdown behavior for active MITM sessions under load.
+- [ ] Add robust error taxonomy and user-facing failure modes.
+
+## Observability
+
+- [x] Debug output is gated behind `MITMConfig#debug`.
+- [ ] Replace ad-hoc debug prints with structured logs for production diagnostics.
+- [ ] Add metrics (handshake failures, generation latency, cache hits/misses, upstream status rates).
+- [ ] Add health/readiness check endpoint or command.
+
+## Testing
+
+- [ ] Unit tests for certificate generator (key generation, CSR, signing, SAN DNS/IP).
+- [ ] Integration tests for browser trust flow (Firefox/Chromium with local CA).
+- [ ] Negative tests (invalid CA files, malformed CONNECT targets, broken cert cache files).
+- [ ] Load/stress tests for concurrent CONNECT traffic and cert generation.
+
+## Operations
+
+- [~] Runtime sample exists (`samples/server_mitm.cr`) and README usage is documented.
+- [ ] Add deployment profile (systemd/service config, restart policy, file permissions).
+- [ ] Add operational runbook (bootstrap CA, trust install, rotation, incident recovery).
+- [ ] Add secure secret management guidance for CA private key.
+
+## Current Assessment
+
+- Overall maturity: **Advanced MVP / Beta**
+- Not yet production-ready due to outstanding hardening, testing depth, and operational controls.

README.md

@@ -73,6 +73,60 @@ server = HTTP::Proxy::Server.new(handlers: [
 end
 ```
 
+#### HTTPS MITM (MVP, CONNECT HTTP/1.1 only)
+
+```crystal
+server = HTTP::Proxy::Server.new
+server.mitm = HTTP::Proxy::Server::MITMConfig.new(
+  ca_certificate_path: "./certs/mitm-ca.crt",
+  ca_private_key_path: "./certs/mitm-ca.key",
+  certificate_cache_dir: "./.mitm-certs",
+  debug: false,
+)
+
+address = server.bind_tcp("127.0.0.1", 8080)
+puts "Listening on http://#{address}"
+server.listen
+```
+
+Notes:
+
+- This enables HTTPS interception for `CONNECT` requests.
+- The certificate authority (CA) used to sign MITM certs must be trusted by clients.
+- This MVP is intended for HTTP/1.1 traffic over CONNECT.
+
+Certificate files:
+
+- `mitm-ca.crt` / `mitm-ca.key`: local CA (trust anchor used to sign dynamic leaf certs).
+- `./.mitm-certs/*.crt` / `./.mitm-certs/*.key`: generated per-host leaf certificates.
+
+Static mode is still available:
+
+- `mitm.crt` / `mitm.key`: a single leaf certificate and key presented by the proxy.
+
+Firefox setup:
+
+- Import `mitm-ca.crt` in **Authorities** and trust it for websites.
+- Do **not** import `mitm.crt` into Authorities.
+
+Server setup:
+
+- Dynamic mode (recommended): pass `mitm-ca.crt` as `ca_certificate_path` and `mitm-ca.key` as `ca_private_key_path`.
+- Static mode: pass `mitm.crt` as `certificate_chain_path` and `mitm.key` as `private_key_path`.
+
+Run dynamic MITM sample:
+
+```bash
+crystal run samples/server_mitm.cr
+```
+
+Useful flags:
+
+- `--ca-cert ./mitm-ca.crt`
+- `--ca-key ./mitm-ca.key`
+- `--cache-dir ./.mitm-certs`
+- `--debug` (enable verbose MITM request/response output)
+
 ### Client
 
 #### Make request with proxy
@@ -112,7 +166,7 @@ puts response.body
 * [x] HTTPS Proxy: CONNECT support
 * [x] Make context.request & context.response writable
 * [x] Basic Authentication
-* [ ] MITM HTTPS Proxy
+* [x] MITM HTTPS Proxy (MVP, CONNECT HTTP/1.1)
 
 ### Proxy client
 

mitm-ca.crt

@@ -0,0 +1,30 @@
+-----BEGIN CERTIFICATE-----
+MIIFITCCAwmgAwIBAgIUKE5Bbf3Q2Y6N9QR1x4yEZPa0pFIwDQYJKoZIhvcNAQEL
+BQAwGDEWMBQGA1UEAwwNTG9jYWwgTUlUTSBDQTAeFw0yNjAyMjcxNTM5MjhaFw0z
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+Y8ZH/T0v0jhMXQgbLRMr2t/Gz/xT
+-----END CERTIFICATE-----

mitm-ca.key

@@ -0,0 +1,52 @@
+-----BEGIN PRIVATE KEY-----
+MIIJQQIBADANBgkqhkiG9w0BAQEFAASCCSswggknAgEAAoICAQDb8uaLhVtvrSso
+3j/G0HJBiz5zMl6zUBnzzLuv0Dhqpyia4t/6qKu8jco4+iW978bjx4LvsNPzM/jq
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+2XDQweSmPKqwgTMSvbabrXiI0Ekm
+-----END PRIVATE KEY-----

samples/server.cr

@@ -2,7 +2,7 @@ require "../src/http_proxy"
 require "option_parser"
 
 host = "127.0.0.1"
-port = 8081
+port = 8080
 
 OptionParser.parse do |opts|
   opts.on("-h HOST", "--host HOST", "define host to run server") do |opt|

samples/server_mitm.cr

@@ -0,0 +1,65 @@
+require "../src/http_proxy"
+require "option_parser"
+
+host = "127.0.0.1"
+port = 8080
+ca_certificate_path = "./mitm-ca.crt"
+ca_private_key_path = "./mitm-ca.key"
+certificate_cache_dir = "./.mitm-certs"
+upstream_insecure = false
+debug = false
+
+OptionParser.parse do |opts|
+  opts.banner = "Usage: crystal run samples/server_mitm.cr -- [arguments]"
+
+  opts.on("-h HOST", "--host HOST", "define host to run server") do |opt|
+    host = opt
+  end
+
+  opts.on("-p PORT", "--port PORT", "define port to run server") do |opt|
+    port = opt.to_i
+  end
+
+  opts.on("--ca-cert PATH", "path to MITM CA certificate PEM (dynamic per-host cert mode)") do |opt|
+    ca_certificate_path = opt
+  end
+
+  opts.on("--ca-key PATH", "path to MITM CA private key PEM (dynamic per-host cert mode)") do |opt|
+    ca_private_key_path = opt
+  end
+
+  opts.on("--cache-dir PATH", "directory to store generated host certificates") do |opt|
+    certificate_cache_dir = opt
+  end
+
+  opts.on("--upstream-insecure", "disable upstream TLS verification") do
+    upstream_insecure = true
+  end
+
+  opts.on("--debug", "enable verbose MITM request/response debug output") do
+    debug = true
+  end
+end
+
+server = HTTP::Proxy::Server.new(handlers: [
+  HTTP::LogHandler.new,
+])
+
+server.mitm = HTTP::Proxy::Server::MITMConfig.new(
+  ca_certificate_path: ca_certificate_path,
+  ca_private_key_path: ca_private_key_path,
+  certificate_cache_dir: certificate_cache_dir,
+  upstream_insecure: upstream_insecure,
+  debug: debug,
+)
+
+address = server.bind_tcp(host, port)
+puts "Listening on http://#{address}"
+puts "MITM mode enabled (CONNECT HTTP/1.1 MVP)"
+puts "Certificate mode: dynamic per-host"
+puts "CA certificate: #{ca_certificate_path}"
+puts "CA private key: #{ca_private_key_path}"
+puts "Certificate cache dir: #{certificate_cache_dir}"
+puts "Upstream TLS verification: #{upstream_insecure ? "DISABLED" : "ENABLED"}"
+puts "MITM debug output: #{debug ? "ENABLED" : "DISABLED"}"
+server.listen

spec/client_spec.cr

@@ -109,8 +109,6 @@ describe HTTP::Proxy::Client do
 
               (client.proxy?).should be_true
               (response.status_code).should eq(407) # 407 Proxy Authentication Required
-
-
             ensure
               wants_close.send(nil)
             end

src/ext/openssl/lib_crypro.cr

@@ -0,0 +1,48 @@
+require "openssl/lib_crypto"
+
+lib LibCrypto
+  alias EVP_PKEY = Void*
+  alias EVP_PKEY_CTX = Void*
+  alias X509_REQ = Void*
+  alias ASN1_INTEGER = Void*
+  alias ASN1_TIME = Void*
+
+  EVP_PKEY_RSA = 6
+
+  fun evp_pkey_ctx_new_id = EVP_PKEY_CTX_new_id(id : Int32, e : Void*) : EVP_PKEY_CTX
+  fun evp_pkey_ctx_free = EVP_PKEY_CTX_free(ctx : EVP_PKEY_CTX)
+  fun evp_pkey_keygen_init = EVP_PKEY_keygen_init(ctx : EVP_PKEY_CTX) : Int32
+  fun evp_pkey_ctx_ctrl_str = EVP_PKEY_CTX_ctrl_str(ctx : EVP_PKEY_CTX, type : UInt8*, value : UInt8*) : Int32
+  fun evp_pkey_keygen = EVP_PKEY_keygen(ctx : EVP_PKEY_CTX, ppkey : EVP_PKEY*) : Int32
+  fun evp_pkey_free = EVP_PKEY_free(pkey : EVP_PKEY)
+
+  fun bio_new_file = BIO_new_file(filename : UInt8*, mode : UInt8*) : Bio*
+  fun bio_free_all = BIO_free_all(bio : Bio*) : Int32
+
+  fun pem_read_bio_private_key = PEM_read_bio_PrivateKey(bp : Bio*, x : EVP_PKEY*, cb : Void*, u : Void*) : EVP_PKEY
+  fun pem_write_bio_private_key = PEM_write_bio_PrivateKey(bp : Bio*, x : EVP_PKEY, enc : Void*, kstr : UInt8*, klen : Int32, cb : Void*, u : Void*) : Int32
+
+  fun pem_read_bio_x509 = PEM_read_bio_X509(bp : Bio*, x : X509*, cb : Void*, u : Void*) : X509
+  fun pem_write_bio_x509_req = PEM_write_bio_X509_REQ(bp : Bio*, x : X509_REQ) : Int32
+  fun pem_write_bio_x509 = PEM_write_bio_X509(bp : Bio*, x : X509) : Int32
+
+  fun x509_req_new = X509_REQ_new : X509_REQ
+  fun x509_req_free = X509_REQ_free(req : X509_REQ)
+  fun x509_req_set_version = X509_REQ_set_version(req : X509_REQ, version : Long) : Int32
+  fun x509_req_set_subject_name = X509_REQ_set_subject_name(req : X509_REQ, name : X509_NAME) : Int32
+  fun x509_req_set_pubkey = X509_REQ_set_pubkey(req : X509_REQ, pkey : EVP_PKEY) : Int32
+  fun x509_req_sign = X509_REQ_sign(req : X509_REQ, pkey : EVP_PKEY, md : EVP_MD) : Int32
+  fun x509_req_get_subject_name = X509_REQ_get_subject_name(req : X509_REQ) : X509_NAME
+  fun x509_req_get_pubkey = X509_REQ_get_pubkey(req : X509_REQ) : EVP_PKEY
+
+  fun x509_set_version = X509_set_version(x : X509, version : Long) : Int32
+  fun x509_set_issuer_name = X509_set_issuer_name(x : X509, name : X509_NAME) : Int32
+  fun x509_set_pubkey = X509_set_pubkey(x : X509, pkey : EVP_PKEY) : Int32
+  fun x509_sign = X509_sign(x : X509, pkey : EVP_PKEY, md : EVP_MD) : Int32
+  fun x509_get_serial_number = X509_get_serialNumber(x : X509) : ASN1_INTEGER
+  fun x509_getm_not_before = X509_getm_notBefore(x : X509) : ASN1_TIME
+  fun x509_getm_not_after = X509_getm_notAfter(x : X509) : ASN1_TIME
+
+  fun asn1_integer_set = ASN1_INTEGER_set(a : ASN1_INTEGER, v : Long) : Int32
+  fun x509_gmtime_adj = X509_gmtime_adj(s : ASN1_TIME, adj : Long) : ASN1_TIME
+end

src/http/proxy/server.cr

@@ -2,6 +2,7 @@ require "socket"
 require "wait_group"
 require "./server/handler"
 require "./server/context"
+require "./server/mitm_config"
 {% if !flag?(:without_openssl) %}
   require "openssl"
 {% end %}
@@ -28,6 +29,8 @@ class HTTP::Proxy::Server
   # Returns `true` if this server is listening on its sockets.
   getter? listening : Bool = false
 
+  property mitm : MITMConfig?
+
   # Creates a new HTTP Proxy server
   def initialize
     handler = build_middleware
@@ -61,7 +64,7 @@ class HTTP::Proxy::Server
   end
 
   private def build_middleware(handler : (Context ->)? = nil)
-    proxy_handler = Handler.new
+    proxy_handler = Handler.new(-> { @mitm })
     proxy_handler.next = handler if handler
     proxy_handler
   end