diff --git a/rust/connlib/phoenix-channel/src/lib.rs b/rust/connlib/phoenix-channel/src/lib.rs
index bf70ea50f..dd6ebcc0e 100644
--- a/rust/connlib/phoenix-channel/src/lib.rs
+++ b/rust/connlib/phoenix-channel/src/lib.rs
@@ -398,6 +398,11 @@ where
                         self.heartbeat.reset();
                         self.state = State::Connected(stream);
 
+                        // Clear local state.
+                        // Joins are only valid whilst we are connected, so we need to discard any previous ones on reconnect.
+                        self.pending_joins.clear();
+                        self.pending_join_requests.clear();
+
                         let (host, _) = self.url_prototype.expose_secret().host_and_port();
 
                         tracing::info!(%host, "Connected to portal");
@@ -512,6 +517,11 @@ where
 
                             continue;
                         }
+                    } else if !self.pending_messages.is_empty() {
+                        tracing::trace!(
+                            requests = ?self.pending_join_requests,
+                            "Unable to send message because we are waiting for JOIN requests to complete"
+                        );
                     }
                 }
                 Poll::Ready(Err(e)) => {
diff --git a/website/src/components/Changelog/Android.tsx b/website/src/components/Changelog/Android.tsx
index ae275c660..b16d1245e 100644
--- a/website/src/components/Changelog/Android.tsx
+++ b/website/src/components/Changelog/Android.tsx
@@ -21,6 +21,11 @@ export default function Android() {
     <Entries downloadLinks={downloadLinks} title="Android">
       {/* When you cut a release, remove any solved issues from the "known issues" lists over in `client-apps`. This must not be done when the issue's PR merges. */}
       <Unreleased>
+        <ChangeItem pull="9985">
+          Fixes an issue where control plane messages could be stuck forever on
+          flaky connections, requiring signing out and signin back in to
+          recover.
+        </ChangeItem>
         <ChangeItem pull="9725">
           Fixes an issue where Firezone failed to sign-in on systems with
           non-ASCII characters in their kernel build name.
diff --git a/website/src/components/Changelog/Apple.tsx b/website/src/components/Changelog/Apple.tsx
index 5bb56063d..0df66b37a 100644
--- a/website/src/components/Changelog/Apple.tsx
+++ b/website/src/components/Changelog/Apple.tsx
@@ -25,6 +25,11 @@ export default function Apple() {
     <Entries downloadLinks={downloadLinks} title="macOS / iOS">
       {/* When you cut a release, remove any solved issues from the "known issues" lists over in `client-apps`. This must not be done when the issue's PR merges. */}
       <Unreleased>
+        <ChangeItem pull="9985">
+          Fixes an issue where control plane messages could be stuck forever on
+          flaky connections, requiring signing out and signin back in to
+          recover.
+        </ChangeItem>
         <ChangeItem pull="9891">
           Fixes an issue where connections would sometimes take up to 90s to
           establish.
diff --git a/website/src/components/Changelog/GUI.tsx b/website/src/components/Changelog/GUI.tsx
index bf2fe3050..29c899493 100644
--- a/website/src/components/Changelog/GUI.tsx
+++ b/website/src/components/Changelog/GUI.tsx
@@ -11,6 +11,11 @@ export default function GUI({ os }: { os: OS }) {
     <Entries downloadLinks={downloadLinks(os)} title={title(os)}>
       {/* When you cut a release, remove any solved issues from the "known issues" lists over in `client-apps`. This must not be done when the issue's PR merges. */}
       <Unreleased>
+        <ChangeItem pull="9985">
+          Fixes an issue where control plane messages could be stuck forever on
+          flaky connections, requiring signing out and signin back in to
+          recover.
+        </ChangeItem>
         <ChangeItem pull="9891">
           Fixes an issue where connections would sometimes take up to 90s to
           establish.
diff --git a/website/src/components/Changelog/Headless.tsx b/website/src/components/Changelog/Headless.tsx
index e062dbbc8..2ff40fd71 100644
--- a/website/src/components/Changelog/Headless.tsx
+++ b/website/src/components/Changelog/Headless.tsx
@@ -10,6 +10,11 @@ export default function Headless({ os }: { os: OS }) {
     <Entries downloadLinks={downloadLinks(os)} title={title(os)}>
       {/* When you cut a release, remove any solved issues from the "known issues" lists over in `client-apps`. This must not be done when the issue's PR merges. */}
       <Unreleased>
+        <ChangeItem pull="9985">
+          Fixes an issue where control plane messages could be stuck forever on
+          flaky connections, requiring signing out and signin back in to
+          recover.
+        </ChangeItem>
         <ChangeItem pull="9891">
           Fixes an issue where connections would sometimes take up to 90s to
           establish.