diff --git a/agent/error_classifier.py b/agent/error_classifier.py
index 14a2609d8..04875b6a5 100644
--- a/agent/error_classifier.py
+++ b/agent/error_classifier.py
@@ -220,12 +220,25 @@ _TRANSPORT_ERROR_TYPES = frozenset({
     "ConnectionAbortedError", "BrokenPipeError",
     "TimeoutError", "ReadError",
     "ServerDisconnectedError",
+    # SSL/TLS transport errors — transient mid-stream handshake/record
+    # failures that should retry rather than surface as a stalled session.
+    # ssl.SSLError subclasses OSError (caught by isinstance) but we list
+    # the type names here so provider-wrapped SSL errors (e.g. when the
+    # SDK re-raises without preserving the exception chain) still classify
+    # as transport rather than falling through to the unknown bucket.
+    "SSLError", "SSLZeroReturnError", "SSLWantReadError",
+    "SSLWantWriteError", "SSLEOFError", "SSLSyscallError",
     # OpenAI SDK errors (not subclasses of Python builtins)
     "APIConnectionError",
     "APITimeoutError",
 })
 
-# Server disconnect patterns (no status code, but transport-level)
+# Server disconnect patterns (no status code, but transport-level).
+# These are the "ambiguous" patterns — a plain connection close could be
+# transient transport hiccup OR server-side context overflow rejection
+# (common when the API gateway disconnects instead of returning an HTTP
+# error for oversized requests).  A large session + one of these patterns
+# triggers the context-overflow-with-compression recovery path.
 _SERVER_DISCONNECT_PATTERNS = [
     "server disconnected",
     "peer closed connection",
@@ -236,6 +249,40 @@ _SERVER_DISCONNECT_PATTERNS = [
     "incomplete chunked read",
 ]
 
+# SSL/TLS transient failure patterns — intentionally distinct from
+# _SERVER_DISCONNECT_PATTERNS above.
+#
+# An SSL alert mid-stream is almost always a transport-layer hiccup
+# (flaky network, mid-session TLS renegotiation failure, load balancer
+# dropping the connection) — NOT a server-side context overflow signal.
+# So we want the retry path but NOT the compression path; lumping these
+# into _SERVER_DISCONNECT_PATTERNS would trigger unnecessary (and
+# expensive) context compression on any large-session SSL hiccup.
+#
+# The OpenSSL library constructs error codes by prepending a format string
+# to the uppercased alert reason; OpenSSL 3.x changed the separator
+# (e.g. `SSLV3_ALERT_BAD_RECORD_MAC` → `SSL/TLS_ALERT_BAD_RECORD_MAC`),
+# which silently stopped matching anything explicit.  Matching on the
+# stable substrings (`bad record mac`, `ssl alert`, `tls alert`, etc.)
+# survives future OpenSSL format churn without code changes.
+_SSL_TRANSIENT_PATTERNS = [
+    # Space-separated (human-readable form, Python ssl module, most SDKs)
+    "bad record mac",
+    "ssl alert",
+    "tls alert",
+    "ssl handshake failure",
+    "tlsv1 alert",
+    "sslv3 alert",
+    # Underscore-separated (OpenSSL error code tokens, e.g.
+    # `ERR_SSL_SSL/TLS_ALERT_BAD_RECORD_MAC`, `SSLV3_ALERT_BAD_RECORD_MAC`)
+    "bad_record_mac",
+    "ssl_alert",
+    "tls_alert",
+    "tls_alert_internal_error",
+    # Python ssl module prefix, e.g. "[SSL: BAD_RECORD_MAC]"
+    "[ssl:",
+]
+
 
 # ── Classification pipeline ─────────────────────────────────────────────
 
@@ -255,9 +302,10 @@ def classify_api_error(
       2. HTTP status code + message-aware refinement
       3. Error code classification (from body)
       4. Message pattern matching (billing vs rate_limit vs context vs auth)
-      5. Transport error heuristics
+      5. SSL/TLS transient alert patterns → retry as timeout
       6. Server disconnect + large session → context overflow
-      7. Fallback: unknown (retryable with backoff)
+      7. Transport error heuristics
+      8. Fallback: unknown (retryable with backoff)
 
     Args:
         error: The exception from the API call.
@@ -388,7 +436,18 @@ def classify_api_error(
     if classified is not None:
         return classified
 
-    # ── 5. Server disconnect + large session → context overflow ─────
+    # ── 5. SSL/TLS transient errors → retry as timeout (not compression) ──
+    # SSL alerts mid-stream are transport hiccups, not server-side context
+    # overflow signals.  Classify before the disconnect check so a large
+    # session doesn't incorrectly trigger context compression when the real
+    # cause is a flaky TLS handshake.  Also matches when the error is
+    # wrapped in a generic exception whose message string carries the SSL
+    # alert text but the type isn't ssl.SSLError (happens with some SDKs
+    # that re-raise without chaining).
+    if any(p in error_msg for p in _SSL_TRANSIENT_PATTERNS):
+        return _result(FailoverReason.timeout, retryable=True)
+
+    # ── 6. Server disconnect + large session → context overflow ─────
     # Must come BEFORE generic transport error catch — a disconnect on
     # a large session is more likely context overflow than a transient
     # transport hiccup.  Without this ordering, RemoteProtocolError
@@ -405,12 +464,12 @@ def classify_api_error(
             )
         return _result(FailoverReason.timeout, retryable=True)
 
-    # ── 6. Transport / timeout heuristics ───────────────────────────
+    # ── 7. Transport / timeout heuristics ───────────────────────────
 
     if error_type in _TRANSPORT_ERROR_TYPES or isinstance(error, (TimeoutError, ConnectionError, OSError)):
         return _result(FailoverReason.timeout, retryable=True)
 
-    # ── 7. Fallback: unknown ────────────────────────────────────────
+    # ── 8. Fallback: unknown ────────────────────────────────────────
 
     return _result(FailoverReason.unknown, retryable=True)
 
diff --git a/tests/agent/test_error_classifier.py b/tests/agent/test_error_classifier.py
index 44e7059a9..c8faffb0c 100644
--- a/tests/agent/test_error_classifier.py
+++ b/tests/agent/test_error_classifier.py
@@ -949,3 +949,94 @@ class TestAdversarialEdgeCases:
         e = MockAPIError("server error", status_code=500, body={"message": None})
         result = classify_api_error(e)
         assert result is not None
+
+
+# ── Test: SSL/TLS transient errors ─────────────────────────────────────
+
+class TestSSLTransientPatterns:
+    """SSL/TLS alerts mid-stream should retry as timeout, not unknown, and
+    should NOT trigger context compression even on a large session.
+
+    Motivation: OpenSSL 3.x changed TLS alert error code format
+    (`SSLV3_ALERT_BAD_RECORD_MAC` → `SSL/TLS_ALERT_BAD_RECORD_MAC`),
+    breaking string-exact matching in downstream retry logic.  We match
+    stable substrings instead.
+    """
+
+    def test_bad_record_mac_classifies_as_timeout(self):
+        """OpenSSL 3.x mid-stream bad record mac alert."""
+        e = Exception("[SSL: BAD_RECORD_MAC] sslv3 alert bad record mac (_ssl.c:2580)")
+        result = classify_api_error(e)
+        assert result.reason == FailoverReason.timeout
+        assert result.retryable is True
+        assert result.should_compress is False
+
+    def test_openssl_3x_format_classifies_as_timeout(self):
+        """New format `ERR_SSL_SSL/TLS_ALERT_BAD_RECORD_MAC` still matches
+        because we key on both space- and underscore-separated forms of
+        the stable `bad_record_mac` token."""
+        e = Exception("ERR_SSL_SSL/TLS_ALERT_BAD_RECORD_MAC during streaming")
+        result = classify_api_error(e)
+        assert result.reason == FailoverReason.timeout
+        assert result.retryable is True
+        assert result.should_compress is False
+
+    def test_tls_alert_internal_error_classifies_as_timeout(self):
+        e = Exception("[SSL: TLSV1_ALERT_INTERNAL_ERROR] tlsv1 alert internal error")
+        result = classify_api_error(e)
+        assert result.reason == FailoverReason.timeout
+        assert result.retryable is True
+        assert result.should_compress is False
+
+    def test_ssl_handshake_failure_classifies_as_timeout(self):
+        e = Exception("ssl handshake failure during mid-stream")
+        result = classify_api_error(e)
+        assert result.reason == FailoverReason.timeout
+        assert result.retryable is True
+
+    def test_ssl_prefix_classifies_as_timeout(self):
+        """Python's generic '[SSL: XYZ]' prefix from the ssl module."""
+        e = Exception("[SSL: UNEXPECTED_EOF_WHILE_READING] EOF occurred in violation of protocol")
+        result = classify_api_error(e)
+        assert result.reason == FailoverReason.timeout
+        assert result.retryable is True
+
+    def test_ssl_alert_on_large_session_does_not_compress(self):
+        """Critical: SSL alerts on big contexts must NOT trigger context
+        compression — compression is expensive and won't fix a transport
+        hiccup.  This is why _SSL_TRANSIENT_PATTERNS is separate from
+        _SERVER_DISCONNECT_PATTERNS.
+        """
+        e = Exception("[SSL: BAD_RECORD_MAC] sslv3 alert bad record mac")
+        result = classify_api_error(
+            e,
+            approx_tokens=180000,      # 90% of a 200k-context window
+            context_length=200000,
+            num_messages=300,
+        )
+        assert result.reason == FailoverReason.timeout
+        assert result.should_compress is False
+
+    def test_plain_disconnect_on_large_session_still_compresses(self):
+        """Regression guard: the context-overflow-via-disconnect path
+        (non-SSL disconnects on large sessions) must still trigger
+        compression.  Only SSL-specific disconnects skip it.
+        """
+        e = Exception("Server disconnected without sending a response")
+        result = classify_api_error(
+            e,
+            approx_tokens=180000,
+            context_length=200000,
+            num_messages=300,
+        )
+        assert result.reason == FailoverReason.context_overflow
+        assert result.should_compress is True
+
+    def test_real_ssl_error_type_classifies_as_timeout(self):
+        """Real ssl.SSLError instance — the type name alone (not message)
+        should route to the transport bucket."""
+        import ssl
+        e = ssl.SSLError("arbitrary ssl error")
+        result = classify_api_error(e)
+        assert result.reason == FailoverReason.timeout
+        assert result.retryable is True