diff --git a/Tests/LibTLS/TestTLSHandshake.cpp b/Tests/LibTLS/TestTLSHandshake.cpp
index 761098c8f9..9494f258e8 100644
--- a/Tests/LibTLS/TestTLSHandshake.cpp
+++ b/Tests/LibTLS/TestTLSHandshake.cpp
@@ -70,10 +70,11 @@ TEST_CASE(test_TLS_hello_handshake)
     tls->set_root_certificates(s_root_ca_certificates);
     bool sent_request = false;
     ByteBuffer contents;
-    tls->on_tls_ready_to_write = [&](TLS::TLSv12& tls) {
+    tls->set_on_tls_ready_to_write([&](TLS::TLSv12& tls) {
         if (sent_request)
             return;
         sent_request = true;
+        Core::deferred_invoke([&tls] { tls.set_on_tls_ready_to_write(nullptr); });
         if (!tls.write("GET / HTTP/1.1\r\nHost: "_b)) {
             FAIL("write(0) failed");
             loop.quit(0);
@@ -87,7 +88,7 @@ TEST_CASE(test_TLS_hello_handshake)
             FAIL("write(2) failed");
             loop.quit(0);
         }
-    };
+    });
     tls->on_tls_ready_to_read = [&](TLS::TLSv12& tls) {
         auto data = tls.read();
         if (!data.has_value()) {
diff --git a/Userland/Libraries/LibGemini/GeminiJob.cpp b/Userland/Libraries/LibGemini/GeminiJob.cpp
index 340d470644..64ff2dbee2 100644
--- a/Userland/Libraries/LibGemini/GeminiJob.cpp
+++ b/Userland/Libraries/LibGemini/GeminiJob.cpp
@@ -93,9 +93,10 @@ void GeminiJob::register_on_ready_to_read(Function<void()> callback)
 
 void GeminiJob::register_on_ready_to_write(Function<void()> callback)
 {
-    m_socket->on_tls_ready_to_write = [callback = move(callback)](auto&) {
+    m_socket->set_on_tls_ready_to_write([callback = move(callback)](auto& tls) {
+        Core::deferred_invoke([&tls] { tls.set_on_tls_ready_to_write(nullptr); });
         callback();
-    };
+    });
 }
 
 bool GeminiJob::can_read_line() const
diff --git a/Userland/Libraries/LibHTTP/HttpsJob.cpp b/Userland/Libraries/LibHTTP/HttpsJob.cpp
index 0f249fc5fb..abaeb662f6 100644
--- a/Userland/Libraries/LibHTTP/HttpsJob.cpp
+++ b/Userland/Libraries/LibHTTP/HttpsJob.cpp
@@ -68,6 +68,7 @@ void HttpsJob::shutdown()
         return;
     m_socket->on_tls_ready_to_read = nullptr;
     m_socket->on_tls_connected = nullptr;
+    m_socket->set_on_tls_ready_to_write(nullptr);
     m_socket = nullptr;
 }
 
@@ -97,9 +98,10 @@ void HttpsJob::register_on_ready_to_read(Function<void()> callback)
 
 void HttpsJob::register_on_ready_to_write(Function<void()> callback)
 {
-    m_socket->on_tls_ready_to_write = [callback = move(callback)](auto&) {
+    m_socket->set_on_tls_ready_to_write([callback = move(callback)](auto& tls) {
+        Core::deferred_invoke([&tls] { tls.set_on_tls_ready_to_write(nullptr); });
         callback();
-    };
+    });
 }
 
 bool HttpsJob::can_read_line() const
diff --git a/Userland/Libraries/LibTLS/TLSv12.h b/Userland/Libraries/LibTLS/TLSv12.h
index e1702c1a1c..1a84f0713e 100644
--- a/Userland/Libraries/LibTLS/TLSv12.h
+++ b/Userland/Libraries/LibTLS/TLSv12.h
@@ -373,8 +373,16 @@ public:
     bool can_read() const { return m_context.application_buffer.size() > 0; }
     String read_line(size_t max_size);
 
+    void set_on_tls_ready_to_write(Function<void(TLSv12&)> function)
+    {
+        on_tls_ready_to_write = move(function);
+        if (on_tls_ready_to_write) {
+            if (is_established())
+                on_tls_ready_to_write(*this);
+        }
+    }
+
     Function<void(TLSv12&)> on_tls_ready_to_read;
-    Function<void(TLSv12&)> on_tls_ready_to_write;
     Function<void(AlertDescription)> on_tls_error;
     Function<void()> on_tls_connected;
     Function<void()> on_tls_finished;
@@ -521,6 +529,7 @@ private:
     i32 m_max_wait_time_for_handshake_in_seconds { 10 };
 
     RefPtr<Core::Timer> m_handshake_timeout_timer;
+    Function<void(TLSv12&)> on_tls_ready_to_write;
 };
 
 }
diff --git a/Userland/Libraries/LibWebSocket/Impl/TLSv12WebSocketConnectionImpl.cpp b/Userland/Libraries/LibWebSocket/Impl/TLSv12WebSocketConnectionImpl.cpp
index 370f77c4eb..b3313ca9e6 100644
--- a/Userland/Libraries/LibWebSocket/Impl/TLSv12WebSocketConnectionImpl.cpp
+++ b/Userland/Libraries/LibWebSocket/Impl/TLSv12WebSocketConnectionImpl.cpp
@@ -33,9 +33,10 @@ void TLSv12WebSocketConnectionImpl::connect(ConnectionInfo const& connection)
     m_socket->on_tls_ready_to_read = [this](auto&) {
         on_ready_to_read();
     };
-    m_socket->on_tls_ready_to_write = [this](auto&) {
+    m_socket->set_on_tls_ready_to_write([this](auto& tls) {
+        tls.set_on_tls_ready_to_write(nullptr);
         on_connected();
-    };
+    });
     m_socket->on_tls_finished = [this] {
         on_connection_error();
     };
diff --git a/Userland/Utilities/test-crypto.cpp b/Userland/Utilities/test-crypto.cpp
index 730ff499aa..1d94219d00 100644
--- a/Userland/Utilities/test-crypto.cpp
+++ b/Userland/Utilities/test-crypto.cpp
@@ -152,12 +152,12 @@ static void tls(const char* message, size_t len)
             if (buffer.has_value())
                 out("{}", StringView { buffer->data(), buffer->size() });
         };
-        tls->on_tls_ready_to_write = [&](auto&) {
+        tls->set_on_tls_ready_to_write([&](auto&) {
             if (write.size()) {
                 tls->write(write);
                 write.clear();
             }
-        };
+        });
         tls->on_tls_error = [&](auto) {
             g_loop.quit(1);
         };
@@ -2013,10 +2013,11 @@ static void tls_test_client_hello()
     tls->set_root_certificates(s_root_ca_certificates);
     bool sent_request = false;
     ByteBuffer contents;
-    tls->on_tls_ready_to_write = [&](TLS::TLSv12& tls) {
+    tls->set_on_tls_ready_to_write([&](TLS::TLSv12& tls) {
         if (sent_request)
             return;
         sent_request = true;
+        Core::deferred_invoke([&tls] { tls.set_on_tls_ready_to_write(nullptr); });
         if (!tls.write("GET / HTTP/1.1\r\nHost: "_b)) {
             FAIL(write(0) failed);
             loop.quit(0);
@@ -2030,7 +2031,7 @@ static void tls_test_client_hello()
             FAIL(write(2) failed);
             loop.quit(0);
         }
-    };
+    });
     tls->on_tls_ready_to_read = [&](TLS::TLSv12& tls) {
         auto data = tls.read();
         if (!data.has_value()) {