diff --git a/CHANGELOG.md b/CHANGELOG.md
index aa9faf2..5c775e0 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -50,6 +50,12 @@
   `close`, so a client sending `CLOSE`, `Close`, or `close, TE` kept the
   socket open and got `Connection: keep-alive` back. The value is now read as
   a list of case-insensitive comma-separated tokens (RFC 9110 §7.6.1).
+- **`Connection: close` is honoured when it arrives on its own header line.**
+  A client sending `Connection: keep-alive` and `Connection: close` as two
+  separate field lines kept the socket open, because only the first line was
+  read. Every `Connection` line is now considered — whatever the case of its
+  field name, so `connection:` from an HTTP/2 downgrading proxy counts too —
+  as RFC 9110 §5.3 requires of repeated field lines.
 
 ## 0.8.0 (2026-07-12)
 
diff --git a/test/web.carp b/test/web.carp
index 08674e0..f9b38ae 100644
--- a/test/web.carp
+++ b/test/web.carp
@@ -541,6 +541,68 @@
     (web-keep-alive? &(parse-req "GET / HTTP/1.0\r\nHost: x\r\n\r\n"))
     "keep-alive? defaults to close on HTTP/1.0 without Connection")
 
+  ; -- repeated Connection field lines (RFC 9110 §5.3) --
+  (assert-false test
+    (web-keep-alive?
+      &(parse-req
+        "GET / HTTP/1.1\r\nConnection: keep-alive\r\nConnection: close\r\n\r\n"))
+    "keep-alive? honors close on a later Connection line")
+
+  (assert-false test
+    (web-keep-alive?
+      &(parse-req
+        "GET / HTTP/1.1\r\nConnection: close\r\nConnection: keep-alive\r\n\r\n"))
+    "keep-alive? honors close on an earlier Connection line")
+
+  (assert-false test
+    (web-keep-alive?
+      &(parse-req
+        "GET / HTTP/1.1\r\nConnection: TE\r\nConnection: Keep-Alive, CLOSE\r\n\r\n"))
+    "keep-alive? honors a close token in any of several Connection lines")
+
+  (assert-true test
+    (web-keep-alive?
+      &(parse-req
+        "GET / HTTP/1.1\r\nConnection: TE\r\nConnection: keep-alive\r\n\r\n"))
+    "keep-alive? true when no Connection line lists close")
+
+  ; -- repeated Connection lines differing in field-name case (RFC 9110 §5.1) --
+  (assert-false test
+    (web-keep-alive?
+      &(parse-req
+        "GET / HTTP/1.1\r\nConnection: close\r\nconnection: keep-alive\r\n\r\n"))
+    "keep-alive? honors close on a differently cased earlier Connection line")
+
+  (assert-false test
+    (web-keep-alive?
+      &(parse-req
+        "GET / HTTP/1.1\r\nconnection: keep-alive\r\nConnection: close\r\n\r\n"))
+    "keep-alive? honors close on a differently cased later Connection line")
+
+  (assert-false test
+    (web-keep-alive?
+      &(parse-req
+        "GET / HTTP/1.1\r\nCONNECTION: close\r\nConnection: keep-alive\r\n\r\n"))
+    "keep-alive? honors close on an upper-case CONNECTION line")
+
+  (assert-false test
+    (web-keep-alive?
+      &(parse-req
+        "GET / HTTP/1.1\r\nConnection: keep-alive\r\nCONNECTION: close\r\n\r\n"))
+    "keep-alive? honors a trailing upper-case CONNECTION: close")
+
+  (assert-false test
+    (web-keep-alive?
+      &(parse-req
+        "GET / HTTP/1.1\r\nConnection: close\r\nconnection: keep-alive\r\nCONNECTION: TE\r\n\r\n"))
+    "keep-alive? honors close among three case variants of Connection")
+
+  (assert-true test
+    (web-keep-alive?
+      &(parse-req
+        "GET / HTTP/1.1\r\nConnection: TE\r\nconnection: keep-alive\r\n\r\n"))
+    "keep-alive? true when no cased Connection variant lists close")
+
   ; -- decode-multipart-request --
   (assert-equal test
     "hello"
diff --git a/web.carp b/web.carp
index 49fc178..751351c 100644
--- a/web.carp
+++ b/web.carp
@@ -1289,15 +1289,30 @@ responses. The `protocols` field lists the subprotocols that this route supports
                                     nl
                                     &(String.to-bytes "http/1.1")))))))
 
+; Case-insensitive header value lookup. Header names in the parsed map
+; preserve original case (RFC 7230 §3.2 says names are case-insensitive).
+(hidden header-values-ci)
+(defn header-values-ci [hdrs name]
+  (let [lower-name &(String.ascii-to-lower name)]
+    (Map.kv-reduce
+      &(fn [acc k v]
+        (if (= &(String.ascii-to-lower k) lower-name)
+          (Array.concat &[acc @v])
+          acc))
+      (the (Array String) [])
+      hdrs)))
+
 (defn web-keep-alive? [req]
-  (let [http11 (= (Request.version req) "HTTP/1.1")
-        conn (match (Request.header req "Connection")
-          (Maybe.Just v) v
-          (Maybe.Nothing) (if http11 @"keep-alive" @"close"))]
-    ; RFC 9110 §7.6.1: connection options are case-insensitive comma-separated tokens
-    (not
-      (Array.any? &(fn [t] (= &(String.trim t) "close"))
-                  &(String.split-by &(String.ascii-to-lower &conn) &[\,])))))
+  (let [conns (header-values-ci (Request.headers req) "Connection")]
+    (if (Array.empty? &conns)
+      (= (Request.version req) "HTTP/1.1")
+      ; RFC 9110 §5.3/§7.6.1: repeated lines form one comma-separated token list
+      (not
+        (Array.any?
+          &(fn [c]
+            (Array.any? &(fn [t] (= &(String.trim t) "close"))
+                        &(String.split-by &(String.ascii-to-lower c) &[\,])))
+          &conns)))))
 
 (defn web-finalize-response [resp keep-alive]
   (let [body-len (String.length (Response.body &resp))
@@ -1411,16 +1426,6 @@ responses. The `protocols` field lists the subprotocols that this route supports
         (when found (break))))
     result))
 
-; Case-insensitive header value lookup. Header names in the parsed map
-; preserve original case (RFC 7230 §3.2 says names are case-insensitive).
-(hidden header-values-ci)
-(defn header-values-ci [hdrs name]
-  (let [lower-name &(String.ascii-to-lower name)]
-    (Map.kv-reduce
-      &(fn [acc k v] (if (= &(String.ascii-to-lower k) lower-name) @v acc))
-      (the (Array String) [])
-      hdrs)))
-
 ; Try to parse a WebSocket upgrade from a raw HTTP buffer. Returns
 ; (Maybe (Pair String (Pair Int (Pair (Maybe String) (Map String String)))))
 ; — the accept key, route index, negotiated protocol, and params — or