diff --git a/Tests/LibTLS/TestTLSHandshake.cpp b/Tests/LibTLS/TestTLSHandshake.cpp
index 4cdc6bcd19..2f42c29fbb 100644
--- a/Tests/LibTLS/TestTLSHandshake.cpp
+++ b/Tests/LibTLS/TestTLSHandshake.cpp
@@ -61,11 +61,7 @@ TEST_CASE(test_TLS_hello_handshake)
     auto tls = TRY_OR_FAIL(TLS::TLSv12::connect(DEFAULT_SERVER, port, move(options)));
     ByteBuffer contents;
     tls->on_ready_to_read = [&] {
-        auto read_bytes = TRY_OR_FAIL(tls->read_some(contents.must_get_bytes_for_writing(4 * KiB)));
-        if (read_bytes.is_empty()) {
-            FAIL("No data received");
-            loop.quit(1);
-        }
+        (void)TRY_OR_FAIL(tls->read_some(contents.must_get_bytes_for_writing(4 * KiB)));
         loop.quit(0);
     };
 
diff --git a/Userland/Libraries/LibHTTP/Job.cpp b/Userland/Libraries/LibHTTP/Job.cpp
index f157dd723a..d038c38999 100644
--- a/Userland/Libraries/LibHTTP/Job.cpp
+++ b/Userland/Libraries/LibHTTP/Job.cpp
@@ -223,8 +223,20 @@ void Job::on_socket_connected()
         }
 
         if (m_socket->is_eof()) {
-            dbgln_if(JOB_DEBUG, "Read failure: Actually EOF!");
-            return deferred_invoke([this] { did_fail(Core::NetworkJob::Error::ProtocolFailed); });
+            // Some servers really like terminating connections by simply closing them (even TLS ones)
+            // to signal end-of-data, if there's no:
+            // - connection
+            // - content-size
+            // - transfer-encoding: chunked
+            // header, simply treat EOF as a termination signal.
+            if (m_headers.contains("connection"sv) || m_content_length.has_value() || m_current_chunk_total_size.has_value()) {
+                dbgln_if(JOB_DEBUG, "Read failure: Actually EOF!");
+                deferred_invoke([this] { did_fail(Core::NetworkJob::Error::ProtocolFailed); });
+                return;
+            }
+
+            finish_up();
+            return;
         }
 
         while (m_state == State::InStatus) {
diff --git a/Userland/Libraries/LibTLS/Socket.cpp b/Userland/Libraries/LibTLS/Socket.cpp
index 90febf9928..9e13824eb9 100644
--- a/Userland/Libraries/LibTLS/Socket.cpp
+++ b/Userland/Libraries/LibTLS/Socket.cpp
@@ -174,6 +174,16 @@ ErrorOr<void> TLSv12::read_from_socket()
         consume(read_bytes);
     } while (!read_bytes.is_empty() && !m_context.critical_error);
 
+    if (read_bytes.is_empty()) {
+        // read_some() returned an empty span, this is either an EOF (from improper closure)
+        // or some sort of weird even that is showing itself as an EOF.
+        // To guard against servers closing the connection weirdly or just improperly, make sure
+        // to check the connection state here and send the appropriate notifications.
+        stream.close();
+
+        check_connection_state(true);
+    }
+
     return {};
 }
 
@@ -204,6 +214,11 @@ bool TLSv12::check_connection_state(bool read)
         m_context.connection_finished = true;
         m_context.connection_status = ConnectionStatus::Disconnected;
         close();
+        m_context.has_invoked_finish_or_error_callback = true;
+        if (on_ready_to_read)
+            on_ready_to_read(); // Notify the client about the weird event.
+        if (on_tls_finished)
+            on_tls_finished();
         return false;
     }
 
@@ -291,7 +306,8 @@ ErrorOr<bool> TLSv12::flush()
 
 void TLSv12::close()
 {
-    alert(AlertLevel::FATAL, AlertDescription::CLOSE_NOTIFY);
+    if (underlying_stream().is_open())
+        alert(AlertLevel::FATAL, AlertDescription::CLOSE_NOTIFY);
     // bye bye.
     m_context.connection_status = ConnectionStatus::Disconnected;
 }