diff --git a/CHANGELOG.md b/CHANGELOG.md
index e2d7d3e53..9c23003f5 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -11,6 +11,7 @@
 
 * [#3020](https://github.com/clojure-emacs/cider/issues/3020): Fix session linking on Windows, e.g. when jumping into a library on the classpath.
 * [#3031](https://github.com/clojure-emacs/cider/pull/3031): Fix `cider-eval-defun-up-to-point` failing to match delimiters correctly in some cases, resulting in reader exceptions.
+* [#3039](https://github.com/clojure-emacs/cider/pull/3039): Allow starting the sideloader for the tooling session
 
 ## 1.1.1 (2021-05-24)
 
diff --git a/cider-client.el b/cider-client.el
index 50f3832d7..528b0a28b 100644
--- a/cider-client.el
+++ b/cider-client.el
@@ -162,13 +162,14 @@ Signal an error if it is not supported."
   (unless (cider-nrepl-op-supported-p op)
     (user-error "`%s' requires the nREPL op \"%s\" (provided by cider-nrepl)" this-command op)))
 
-(defun cider-nrepl-send-request (request callback &optional connection)
+(defun cider-nrepl-send-request (request callback &optional connection tooling)
   "Send REQUEST and register response handler CALLBACK.
 REQUEST is a pair list of the form (\"op\" \"operation\" \"par1-name\"
                                     \"par1\" ... ).
 If CONNECTION is provided dispatch to that connection instead of
-the current connection.  Return the id of the sent message."
-  (nrepl-send-request request callback (or connection (cider-current-repl 'any 'ensure))))
+the current connection.  Return the id of the sent message.
+If TOOLING is truthy then the tooling session is used."
+  (nrepl-send-request request callback (or connection (cider-current-repl 'any 'ensure)) tooling))
 
 (defun cider-nrepl-send-sync-request (request &optional connection abort-on-input)
   "Send REQUEST to the nREPL server synchronously using CONNECTION.
diff --git a/cider-eval.el b/cider-eval.el
index 6c635b4af..34a29b246 100644
--- a/cider-eval.el
+++ b/cider-eval.el
@@ -208,13 +208,16 @@ When invoked with a prefix ARG the command doesn't prompt for confirmation."
           (when (member "sideloader-lookup" status)
             (cider-request:sideloader-provide id type name))))))
 
-(defun cider-request:sideloader-start (&optional connection)
+(defun cider-request:sideloader-start (&optional connection tooling)
   "Perform the nREPL \"sideloader-start\" op.
-If CONNECTION is nil, use `cider-current-repl'."
+If CONNECTION is nil, use `cider-current-repl'.
+If TOOLING is truthy then the operation is perfomed over the tooling
+session, rather than the regular session."
   (cider-ensure-op-supported "sideloader-start")
   (cider-nrepl-send-request `("op" "sideloader-start")
                             (cider-sideloader-lookup-handler)
-                            connection))
+                            connection
+                            tooling))
 
 (defun cider-request:sideloader-provide (id type file &optional connection)
   "Perform the nREPL \"sideloader-provide\" op for ID, TYPE and FILE.