diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1e83c9bba..6a33b16ef 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -176,6 +176,7 @@
 
 ### Changes
 
+- [#3567](https://github.com/clojure-emacs/cider/pull/3567): Fix remote `cider-jack-in-clj` breaking with `cider-enrich-classpath` when `clojure.sh|lein.sh` are not available on the remote.
 - CIDER [Inspector](https://docs.cider.mx/cider/debugging/inspector.html): display Java class/method/field info when available.
   - This info is available when [enrich-classpath](https://docs.cider.mx/cider/config/basic_config.html#use-enrich-classpath) is active.
 - [#3495](https://github.com/clojure-emacs/cider/issues/3495): possibly display error overlays on [`cider-load-buffer`](https://docs.cider.mx/cider/usage/code_evaluation.html#basic-evaluation).
diff --git a/cider-util.el b/cider-util.el
index 4cd424439..6b47086f1 100644
--- a/cider-util.el
+++ b/cider-util.el
@@ -529,7 +529,63 @@ Any other value is just returned."
       (mapcar #'cider--deep-vector-to-list x)
     x))
 
+
+;;; Files & Directories
+(defun cider--ensure-executable (file)
+  "Try to make FILE executable if it isn't already.
+Returns FILE on success, nil on failure."
+  (with-demoted-errors "Error while trying to make file executable:\n %s"
+    (when (or (file-executable-p file)
+              (and (set-file-modes file "u+x")
+                   (file-executable-p file)))
+      file)))
+
+(defconst cider--temp-name-prefix ".cider__"
+  "Prefix for marking temporary files created by cider.")
+
+(defun cider--make-temp-name (file)
+  "Generate a randomized name from FILEs basename.
+Tag it with `cider--temp-name-prefix'"
+  (make-temp-name
+   (concat cider--temp-name-prefix (file-name-nondirectory file) "__")))
+
+(defun cider--make-nearby-temp-copy (file)
+  "Create a copy of FILE in the default local or remote tempdir.
+Falls back to `clojure-project-dir' or `default-directory'.
+The copy is marked with `cider--temp-name-prefix'."
+  (let* ((default-directory (or (clojure-project-dir) default-directory))
+         (new-file (file-name-concat (temporary-file-directory)
+                                     (cider--make-temp-name file))))
+    (copy-file file new-file :exists-ok nil nil :keep-permissions)
+    new-file))
+
+(defun cider--inject-self-delete (bash-file)
+  "Make BASH-FILE delete itself on exit.
+Injects the self-delete script after the first line, assuming it is a
+shebang."
+  (let (;; Don't create any temporary files.
+        (remote-file-name-inhibit-locks t)
+        (make-backup-files nil)
+        (auto-save-default nil)
+        ;; Disable version-control check
+        (vc-handled-backends nil))
+    (with-temp-buffer
+      (insert-file-contents bash-file)
+      ;; inject after the first line, assuming it is the shebang
+      (goto-char (point-min))
+      (skip-chars-forward "^\n")
+      (insert "\n")
+      (insert (format
+               "trap 'ARG=$?
+                 rm -v %s
+                 echo \"cider: Cleaned up temporary script after use.\"
+                 exit $ARG
+               ' EXIT"
+               (file-local-name bash-file)))
+      (write-file bash-file))
+    bash-file))
 
+
 ;;; Help mode
 
 ;; Same as https://github.com/emacs-mirror/emacs/blob/86d083438dba60dc00e9e96414bf7e832720c05a/lisp/help-mode.el#L355
diff --git a/cider.el b/cider.el
index 80cdb402b..e4621ca3c 100644
--- a/cider.el
+++ b/cider.el
@@ -452,40 +452,58 @@ without interfering with classloaders."
   :package-version '(cider . "1.2.0")
   :safe #'booleanp)
 
-(defun cider--get-enrich-classpath-lein-script ()
-  "Returns the location of enrich-classpath's lein.sh wrapper script."
-  (when-let ((cider-location (locate-library "cider.el" t)))
-    (concat (file-name-directory cider-location)
-            "lein.sh")))
-
-(defun cider--get-enrich-classpath-clojure-cli-script ()
-  "Returns the location of enrich-classpath's clojure.sh wrapper script."
-  (when-let ((cider-location (locate-library "cider.el" t)))
-    (concat (file-name-directory cider-location)
-            "clojure.sh")))
+(defvar cider--enrich-classpath-script-names
+  '((lein . "lein.sh")
+    (clojure-cli . "clojure.sh")))
+
+(defun cider--enriched-cmd-p (cmd)
+  "Test if the shell-quoted CMD contains the name of an enrich-classpath script."
+  (let* ((script-names (map-values cider--enrich-classpath-script-names))
+         (temp-prefix cider--temp-name-prefix)
+         (any-name  (rx-to-string
+                     `(or (: (or ,@script-names) (or eos space))
+                          (: ,temp-prefix (or ,@script-names))))))
+    (string-match any-name cmd)))
+
+(defun cider--get-enrich-classpath-script (project-type)
+  "Get or create an executable enrich-classpath script for PROJECT-TYPE.
+If `default-directory' is remote, create a copy at
+'<remote-tempdir>/.cider__<script-name>__<random>' that deletes itself after
+use.  The search for '<remote-tempdir>' is handled by tramp and falls back to
+`clojure-project-dir' or `default-directory'.  Returns nil if anything goes wrong."
+  (when-let* ((cider-dir (file-name-directory (locate-library "cider.el" t)))
+              (name (map-elt cider--enrich-classpath-script-names project-type))
+              (location (concat cider-dir name))
+              (script (cider--ensure-executable location)))
+    (if (file-remote-p default-directory)
+        (with-demoted-errors
+            "cider: Failed to initialize enrich-classpath on remote:\n %s"
+          (thread-first
+            (cider--make-nearby-temp-copy script)
+            (cider--ensure-executable)
+            (cider--inject-self-delete)))
+      script)))
+
+(defun cider--jack-in-resolve-command-enrich (project-type)
+  "Conditionally wrap the command for PROJECT-TYPE with an enrich-classpath script.
+Resolves to the non-wrapped `cider-jack-in-command' if `cider-enrich-classpath' is nil or the
+  wrapper-script can't be initialized."
+  (when-let ((command (cider--resolve-command (cider-jack-in-command project-type))))
+    (if-let ((wrapper-script (and cider-enrich-classpath
+                                  (not (eq system-type 'windows-nt))
+                                  (cider--get-enrich-classpath-script project-type))))
+        (concat "bash "
+                (shell-quote-argument (file-local-name wrapper-script)) " "
+                command)
+      command)))
 
 (defun cider-jack-in-resolve-command (project-type)
   "Determine the resolved file path to `cider-jack-in-command'.
 Throws an error if PROJECT-TYPE is unknown."
   (pcase project-type
-    ('lein (let ((r (cider--resolve-command cider-lein-command)))
-             (if (and cider-enrich-classpath
-                      (not (eq system-type 'windows-nt))
-                      (executable-find (cider--get-enrich-classpath-lein-script)))
-                 (concat "bash " ;; don't assume lein.sh is executable - MELPA might change that
-                         (cider--get-enrich-classpath-lein-script)
-                         " "
-                         r)
-               r)))
+    ('lein (cider--jack-in-resolve-command-enrich 'lein))
     ('boot (cider--resolve-command cider-boot-command))
-    ('clojure-cli (if (and cider-enrich-classpath
-                           (not (eq system-type 'windows-nt))
-                           (executable-find (cider--get-enrich-classpath-clojure-cli-script)))
-                      (concat "bash " ;; don't assume clojure.sh is executable - MELPA might change that
-                              (cider--get-enrich-classpath-clojure-cli-script)
-                              " "
-                              (cider--resolve-command cider-clojure-cli-command))
-                    (cider--resolve-command cider-clojure-cli-command)))
+    ('clojure-cli  (cider--jack-in-resolve-command-enrich 'clojure-cli))
     ('babashka (cider--resolve-command cider-babashka-command))
     ;; here we have to account for the possibility that the command is either
     ;; "npx shadow-cljs" or just "shadow-cljs"
@@ -1713,7 +1731,11 @@ PARAMS is a plist with the following keys (non-exhaustive list)
              (command-resolved (cider-jack-in-resolve-command project-type))
              ;; TODO: global-options are deprecated and should be removed in CIDER 2.0
              (command-global-opts (cider-jack-in-global-options project-type))
-             (command-params (cider-jack-in-params project-type)))
+             (command-params (cider-jack-in-params project-type))
+             ;; ignore `cider-enrich-classpath' if the jack-in-command does not include
+             ;; the necessary wrapper script at this point
+             (cider-enrich-classpath (and cider-enrich-classpath
+                                          (cider--enriched-cmd-p command-resolved))))
         (if command-resolved
             (with-current-buffer (or (plist-get params :--context-buffer)
                                      (current-buffer))
@@ -2165,13 +2187,11 @@ M-2 \\[cider-jack-in-universal]."
       (cider-jack-in-clj arg))))
 
 
-;; TODO: Implement a check for command presence over tramp
 (defun cider--resolve-command (command)
-  "Find COMMAND in exec path (see variable `exec-path').
-Return nil if not found.  In case `default-directory' is non-local we
-assume the command is available."
-  (when-let* ((command (or (and (file-remote-p default-directory) command)
-                           (executable-find command)
+  "Test if COMMAND exists, is executable and shell-quote it.
+Return nil otherwise.  When `default-directory' is remote, the check is
+performed by tramp."
+  (when-let* ((command (or (executable-find command :remote)
                            (executable-find (concat command ".bat")))))
     (shell-quote-argument command)))
 
diff --git a/test/cider-tests.el b/test/cider-tests.el
index b7298e36b..95fd9c0ed 100644
--- a/test/cider-tests.el
+++ b/test/cider-tests.el
@@ -106,6 +106,37 @@
               :and-return-value '())
       (expect (cider-project-type) :to-equal cider-jack-in-default))))
 
+(describe "cider--enriched-cmd-p"
+  (describe "when cmd does not contain the path to an enrich-classpath script"
+    (it "returns nil"
+      (expect (cider--enriched-cmd-p "/usr/bin/lein")
+              :to-equal nil)
+      (expect (cider--enriched-cmd-p "bash /usr/bin/lein")
+              :to-equal nil)))
+  (describe "for different path + script-name combinations"
+    :var* ((paths `("/simple/path/"
+                    ,"/tmp/path/ with spaces/"
+                    ,"/ssh:!slightly@cra --zy!path #enrich me/"))
+           (simple-names (map-values cider--enrich-classpath-script-names))
+           (tmp-names (mapcar (lambda (s) (cider--make-temp-name s)) simple-names))
+           (all-names (seq-concatenate 'list simple-names tmp-names)))
+    (cl-loop
+     for path in paths do
+     (cl-loop
+      for name in all-names do
+      (describe (format "cider--enriched-cmd-p with script: %s" (shell-quote-argument (concat path name)))
+        :var ((script (shell-quote-argument (concat path name))))
+        (it "is true in basic cases "
+          (expect (cider--enriched-cmd-p (concat "bash " script " /usr/bin/lein"))
+                  :to-be-truthy)
+          (expect (cider--enriched-cmd-p (concat "TEST=1 bash " script " /usr/bin/env lein"))
+                  :to-be-truthy))
+        (it "handles a fully constructed jack-in-cmd."
+          ;; TODO is it worth generating this?
+          (let ((cmd (concat "bash " script  " /usr/local/bin/lein update-in :dependencies conj \[nrepl/nrepl\ \"1.0.0\"\] -- update-in :plugins conj \[cider/cider-nrepl\ \"0.43.0\"\] -- update-in :plugins conj \[mx.cider/lein-enrich-classpath\ \"1.18.2\"\] -- update-in :middleware conj cider.enrich-classpath.plugin-v2/middleware -- repl :headless :host localhost")))
+            (expect (cider--enriched-cmd-p cmd)
+                    :to-be-truthy))))))))
+
 ;;; cider-jack-in tests
 (describe "cider--gradle-dependency-notation"
   (it "returns a GAV when given a two-element list"