diff --git a/include/openssl/ssl.h b/include/openssl/ssl.h
index 0b98b11..b42e907 100644
--- a/include/openssl/ssl.h
+++ b/include/openssl/ssl.h
@@ -1565,14 +1565,12 @@
 OPENSSL_EXPORT size_t SSL_CTX_sess_number(const SSL_CTX *ctx);
 
 /* SSL_CTX_add_session inserts |session| into |ctx|'s internal session cache. It
- * returns one on success and zero on error or if |ctx| already included a
- * session with that session ID. The caller retains its reference to
- * |session|. */
+ * returns one on success and zero on error or if |session| is already in the
+ * cache. The caller retains its reference to |session|. */
 OPENSSL_EXPORT int SSL_CTX_add_session(SSL_CTX *ctx, SSL_SESSION *session);
 
 /* SSL_CTX_remove_session removes |session| from |ctx|'s internal session cache.
- * It returns one on success and zero on error or if no session with a matching
- * ID was found. */
+ * It returns one on success and zero if |session| was not in the cache. */
 OPENSSL_EXPORT int SSL_CTX_remove_session(SSL_CTX *ctx, SSL_SESSION *session);
 
 /* SSL_CTX_flush_sessions removes all sessions from |ctx| which have expired as
diff --git a/ssl/ssl_session.c b/ssl/ssl_session.c
index 6b17eed..25fe1e8 100644
--- a/ssl/ssl_session.c
+++ b/ssl/ssl_session.c
@@ -382,6 +382,7 @@
     if (session != NULL) {
       SSL_SESSION_up_ref(session);
     }
+    /* TODO(davidben): This should probably move it to the front of the list. */
     CRYPTO_MUTEX_unlock(&ssl->initial_ctx->lock);
 
     if (session != NULL) {
diff --git a/ssl/ssl_test.cc b/ssl/ssl_test.cc
index 875fac8..d2e63a1 100644
--- a/ssl/ssl_test.cc
+++ b/ssl/ssl_test.cc
@@ -15,6 +15,7 @@
 #include <stdio.h>
 #include <string.h>
 
+#include <algorithm>
 #include <string>
 #include <vector>
 
@@ -819,6 +820,157 @@
   return SSL_get_client_CA_list(ssl.get()) == stack;
 }
 
+static void AppendSession(SSL_SESSION *session, void *arg) {
+  std::vector<SSL_SESSION*> *out =
+      reinterpret_cast<std::vector<SSL_SESSION*>*>(arg);
+  out->push_back(session);
+}
+
+// ExpectCache returns true if |ctx|'s session cache consists of |expected|, in
+// order.
+static bool ExpectCache(SSL_CTX *ctx,
+                        const std::vector<SSL_SESSION*> &expected) {
+  // Check the linked list.
+  SSL_SESSION *ptr = ctx->session_cache_head;
+  for (SSL_SESSION *session : expected) {
+    if (ptr != session) {
+      return false;
+    }
+    // TODO(davidben): This is an absurd way to denote the end of the list.
+    if (ptr->next ==
+        reinterpret_cast<SSL_SESSION *>(&ctx->session_cache_tail)) {
+      ptr = nullptr;
+    } else {
+      ptr = ptr->next;
+    }
+  }
+  if (ptr != nullptr) {
+    return false;
+  }
+
+  // Check the hash table.
+  std::vector<SSL_SESSION*> actual, expected_copy;
+  lh_SSL_SESSION_doall_arg(SSL_CTX_sessions(ctx), AppendSession, &actual);
+  expected_copy = expected;
+
+  std::sort(actual.begin(), actual.end());
+  std::sort(expected_copy.begin(), expected_copy.end());
+
+  return actual == expected_copy;
+}
+
+static ScopedSSL_SESSION CreateTestSession(uint32_t number) {
+  ScopedSSL_SESSION ret(SSL_SESSION_new());
+  if (!ret) {
+    return nullptr;
+  }
+
+  ret->session_id_length = SSL3_SSL_SESSION_ID_LENGTH;
+  memset(ret->session_id, 0, ret->session_id_length);
+  memcpy(ret->session_id, &number, sizeof(number));
+  return ret;
+}
+
+// TODO(davidben): Switch this to a |std::vector<ScopedSSL_SESSION>| once we can
+// rely on a move-aware |std::vector|.
+template <class T>
+class ScopedVector {
+ public:
+  explicit ScopedVector(std::vector<T*> *v) : v_(v) {}
+
+  ~ScopedVector() {
+    for (T *t : *v_) {
+      delete t;
+    }
+  }
+
+ private:
+  std::vector<T*> *const v_;
+};
+
+// Test that the internal session cache behaves as expected.
+static bool TestInternalSessionCache() {
+  ScopedSSL_CTX ctx(SSL_CTX_new(TLS_method()));
+  if (!ctx) {
+    return false;
+  }
+
+  // Prepare 10 test sessions.
+  std::vector<SSL_SESSION*> sessions;
+  ScopedVector<SSL_SESSION> cleanup(&sessions);
+  for (int i = 0; i < 10; i++) {
+    ScopedSSL_SESSION session = CreateTestSession(i);
+    if (!session) {
+      return false;
+    }
+    sessions.push_back(session.release());
+  }
+
+  SSL_CTX_sess_set_cache_size(ctx.get(), 5);
+
+  // Insert all the test sessions.
+  for (SSL_SESSION *session : sessions) {
+    if (!SSL_CTX_add_session(ctx.get(), session)) {
+      return false;
+    }
+  }
+
+  // Only the last five should be in the list.
+  std::vector<SSL_SESSION*> expected;
+  expected.push_back(sessions[9]);
+  expected.push_back(sessions[8]);
+  expected.push_back(sessions[7]);
+  expected.push_back(sessions[6]);
+  expected.push_back(sessions[5]);
+  if (!ExpectCache(ctx.get(), expected)) {
+    return false;
+  }
+
+  // Inserting an element already in the cache should fail.
+  if (SSL_CTX_add_session(ctx.get(), sessions[7]) ||
+      !ExpectCache(ctx.get(), expected)) {
+    return false;
+  }
+
+  // Although collisions should be impossible (256-bit session IDs), the cache
+  // must handle them gracefully.
+  ScopedSSL_SESSION collision(CreateTestSession(7));
+  if (!collision || !SSL_CTX_add_session(ctx.get(), collision.get())) {
+    return false;
+  }
+  expected.clear();
+  expected.push_back(collision.get());
+  expected.push_back(sessions[9]);
+  expected.push_back(sessions[8]);
+  expected.push_back(sessions[6]);
+  expected.push_back(sessions[5]);
+  if (!ExpectCache(ctx.get(), expected)) {
+    return false;
+  }
+
+  // Removing sessions behaves correctly.
+  if (!SSL_CTX_remove_session(ctx.get(), sessions[6])) {
+    return false;
+  }
+  expected.clear();
+  expected.push_back(collision.get());
+  expected.push_back(sessions[9]);
+  expected.push_back(sessions[8]);
+  expected.push_back(sessions[5]);
+  if (!ExpectCache(ctx.get(), expected)) {
+    return false;
+  }
+
+  // Removing sessions requires an exact match.
+  if (SSL_CTX_remove_session(ctx.get(), sessions[0]) ||
+      SSL_CTX_remove_session(ctx.get(), sessions[7]) ||
+      !ExpectCache(ctx.get(), expected)) {
+    return false;
+  }
+
+  return true;
+}
+
 int main() {
   CRYPTO_library_init();
 
@@ -839,7 +991,8 @@
       !TestDefaultVersion(DTLS1_2_VERSION, &DTLSv1_2_method) ||
       !TestCipherGetRFCName() ||
       !TestPaddingExtension() ||
-      !TestClientCAList()) {
+      !TestClientCAList() ||
+      !TestInternalSessionCache()) {
     ERR_print_errors_fp(stderr);
     return 1;
   }