diff --git a/e2e/test/scenarios/custom-column/custom-column-reproductions.cy.spec.js b/e2e/test/scenarios/custom-column/custom-column-reproductions.cy.spec.js
index da59a0e526132b4d66610a36bd70bb4896d16cf9..f354bd92fa03850c3985b5186c0e6614a3c9d679 100644
--- a/e2e/test/scenarios/custom-column/custom-column-reproductions.cy.spec.js
+++ b/e2e/test/scenarios/custom-column/custom-column-reproductions.cy.spec.js
@@ -318,8 +318,7 @@ describe("issue 18747", () => {
   function addValueToParameterFilter() {
     filterWidget().click();
     popover().within(() => {
-      cy.findByRole("textbox").type("14");
-      cy.findByText("14").click();
+      cy.findByRole("searchbox").type("14");
       cy.button("Add filter").click();
     });
   }
diff --git a/e2e/test/scenarios/filters-reproductions/dashboard-filters-reproductions.cy.spec.js b/e2e/test/scenarios/filters-reproductions/dashboard-filters-reproductions.cy.spec.js
index a6dca526c8384f87832d08c53ba2841dfaf4bbd6..b9053b7948dafb342e557ae643cc042c8caf2f88 100644
--- a/e2e/test/scenarios/filters-reproductions/dashboard-filters-reproductions.cy.spec.js
+++ b/e2e/test/scenarios/filters-reproductions/dashboard-filters-reproductions.cy.spec.js
@@ -1239,8 +1239,10 @@ describe("issue 22788", () => {
 
   function addFilterAndAssert() {
     filterWidget().click();
-    popover().findByText("Gizmo").click();
-    cy.button("Add filter").click();
+    popover().within(() => {
+      cy.findByRole("searchbox").type("Gizmo");
+      cy.button("Add filter").click();
+    });
 
     cy.findAllByText("Gizmo");
     cy.findAllByText("Doohickey").should("not.exist");
@@ -2130,8 +2132,10 @@ describe("issue 27768", () => {
     saveDashboard();
 
     filterWidget().click();
-    popover().findByText("Gizmo").click();
-    cy.button("Add filter").click();
+    popover().within(() => {
+      cy.findByRole("searchbox").type("Gizmo");
+      cy.button("Add filter").click();
+    });
 
     cy.findAllByText("Doohickey").should("not.exist");
 
diff --git a/src/metabase/lib/expression.cljc b/src/metabase/lib/expression.cljc
index 15bb6b676da6c3e49666f5ab32530b7acb94d19e..6bb03a6211d4eb85331a311a29ca24c5c2d9eb27 100644
--- a/src/metabase/lib/expression.cljc
+++ b/src/metabase/lib/expression.cljc
@@ -297,6 +297,13 @@
    expression-definition :- ::lib.schema.expression/expression]
   (let [expression-name (lib.util/expression-name expression-definition)]
     (-> (lib.metadata.calculation/metadata query stage-number expression-definition)
+        ;; We strip any properties a general expression cannot have, e.g. `:id` and
+        ;; `:join-alias`. Keeping all properties a field can have would make it difficult
+        ;; to distinguish the field column from an expression aliasing that field down the
+        ;; line. It also doesn't make sense to keep the ID and the join alias, as they are
+        ;; not the properties of the expression.
+        (select-keys [:base-type :effective-type :lib/desired-column-alias
+                      :lib/source-column-alias :lib/source-uuid :lib/type])
         (assoc :lib/source   :source/expressions
                :name         expression-name
                :display-name expression-name))))
diff --git a/test/metabase/lib/equality_test.cljc b/test/metabase/lib/equality_test.cljc
index 9cc4b106c672988f1597880afdee7a7d3f6488df..76c99184d46c88e56f91fc9adf9d0aa806a11753 100644
--- a/test/metabase/lib/equality_test.cljc
+++ b/test/metabase/lib/equality_test.cljc
@@ -602,16 +602,15 @@
                (:name (lib.equality/find-matching-column query -1 (lib/ref col) returned))))))))
 
 (deftest ^:parallel field-refs-to-custom-expressions-test
-  (testing "custom columns that wrap a Field have `:id` - prefer matching `[:field {} 7]` to the regular field (#35839)"
+  (testing "custom columns that wrap a Field must not have `:id` (#44940)"
     (let [query      (-> (lib/query meta/metadata-provider (meta/table-metadata :orders))
                          (lib/expression "CA" (meta/field-metadata :orders :created-at)))
           columns    (lib/visible-columns query)
           created-at (m/find-first #(= (:name %) "CREATED_AT") columns)
           ca-expr    (m/find-first #(= (:name %) "CA") columns)]
       (testing "different columns"
-        (is (not= created-at ca-expr))
-        (testing "but both have the ID"
-          (is (= (:id created-at) (:id ca-expr)))))
+        (is (int? (:id created-at)))
+        (is (nil? (:id ca-expr))))
 
       (testing "both refs should match correctly"
         (is (= created-at
@@ -651,3 +650,16 @@
                 (lib/ref col)
                 [total-10
                  total-20])))))))
+
+(deftest ^:parallel find-matching-column-by-id-with-expression-aliasing-joined-column-test
+  (testing "find-matching-column should be able to find columns based on ID even when a joined column is aliased as an expression (#44940)"
+    (let [a-ref [:field {:lib/uuid (str (random-uuid))
+                         :base-type :type/Text
+                         :join-alias "Cat"}
+                 (meta/id :categories :name)]
+          query (-> lib.tu/query-with-join
+                    (lib/expression "Joied Name" a-ref))
+          cols  (lib/returned-columns query)]
+      (is (=? {:name "NAME"
+               :id (meta/id :categories :name)}
+              (lib.equality/find-matching-column query -1 a-ref cols))))))