diff --git a/packages/services/src/kernel/default.ts b/packages/services/src/kernel/default.ts
index 6359c99404c2..a09eb89a06b5 100644
--- a/packages/services/src/kernel/default.ts
+++ b/packages/services/src/kernel/default.ts
@@ -376,13 +376,42 @@ export class KernelConnection implements Kernel.IKernelConnection {
    *
    * If queue is true, queue the message for later sending if we cannot send
    * now. Otherwise throw an error.
+   *
+   * #### Notes
+   * As an exception to the queueing, if we are sending a kernel_info_request
+   * message while we think the kernel is restarting, we send the message
+   * immediately without queueing. This is so that we can trigger a message
+   * back, which will then clear the kernel restarting state.
    */
   private _sendMessage(msg: KernelMessage.IMessage, queue = true) {
     if (this.status === 'dead') {
       throw new Error('Kernel is dead');
     }
 
-    // Send if the ws allows it, otherwise buffer the message.
+    // If we have a kernel_info_request and we are restarting, send the
+    // kernel_info_request immediately if we can, and if not throw an error so
+    // we can retry later. We do this because we must get at least one message
+    // from the kernel to reset the kernel session (thus clearing the restart
+    // status sentinel).
+    if (
+      this._kernelSession === RESTARTING_KERNEL_SESSION &&
+      KernelMessage.isInfoRequestMsg(msg)
+    ) {
+      if (this.connectionStatus === 'connected') {
+        this._ws!.send(serialize.serialize(msg));
+        return;
+      } else {
+        throw new Error('Could not send message: status is not connected');
+      }
+    }
+
+    // If there are pending messages, add to the queue so we keep messages in order
+    if (queue && this._pendingMessages.length > 0) {
+      this._pendingMessages.push(msg);
+      return;
+    }
+
+    // Send if the ws allows it, otherwise queue the message.
     if (
       this.connectionStatus === 'connected' &&
       this._kernelSession !== RESTARTING_KERNEL_SESSION
@@ -1258,29 +1287,17 @@ export class KernelConnection implements Kernel.IKernelConnection {
 
     if (this.status !== 'dead') {
       if (connectionStatus === 'connected') {
-        let restarting = false;
-        if (this._kernelSession === RESTARTING_KERNEL_SESSION) {
-          // Reset kernelSession on new connections,
-          // so we can start sending messages.
-          // Otherwise, requests are queued forever until we get a ws message
-          // that we did not ask for.
-          this._kernelSession = '';
-          restarting = true;
-        }
+        let restarting = this._kernelSession === RESTARTING_KERNEL_SESSION;
 
-        // Send pending messages, and make sure we send at least one message
-        // to get kernel status back.
-        // always request kernel info first, to get kernel status back
-        // and ensure iopub is fully established
+        // Send a kernel info request to make sure we send at least one
+        // message to get kernel status back. Always request kernel info
+        // first, to get kernel status back and ensure iopub is fully
+        // established. If we are restarting, this message will skip the queue
+        // and be sent immediately.
         let p = this.requestKernelInfo();
-        if (restarting) {
-          // preserve restarting state until a reply is received
-          // so messages don't hop ahead of the pending queue
-          // while we are waiting for the kernelInfoReply
-          this._kernelSession = RESTARTING_KERNEL_SESSION;
-        }
-        // only after kernelInfo resolves (or after a timeout)
-        // start sending our pending messages, if any
+
+        // Send any pending messages after the kernelInfo resolves, or after a
+        // timeout as a failsafe.
 
         let sendPendingCalled = false;
         let sendPendingOnce = () => {
@@ -1289,8 +1306,11 @@ export class KernelConnection implements Kernel.IKernelConnection {
           }
           sendPendingCalled = true;
           if (restarting && this._kernelSession === RESTARTING_KERNEL_SESSION) {
-            // we were restarting and a message didn't arrive to set the session
-            // it would be better to retry here
+            // We were restarting and a message didn't arrive to set the
+            // session, but we just assume the restart succeeded and send any
+            // pending messages.
+
+            // FIXME: it would be better to retry the kernel_info_request here
             this._kernelSession = '';
           }
           clearTimeout(timeoutHandle);
@@ -1317,11 +1337,6 @@ export class KernelConnection implements Kernel.IKernelConnection {
   private async _handleMessage(msg: KernelMessage.IMessage): Promise<void> {
     let handled = false;
 
-    if (msg.header.msg_type === 'shutdown_reply') {
-      this._kernelSession = msg.header.session;
-      this._sendPending();
-    }
-
     // Check to see if we have a display_id we need to reroute.
     if (
       msg.parent_header &&