diff --git a/app/models/concerns/category_hashtag.rb b/app/models/concerns/category_hashtag.rb
index 135a903aee9..00f4e3e74f3 100644
--- a/app/models/concerns/category_hashtag.rb
+++ b/app/models/concerns/category_hashtag.rb
@@ -46,18 +46,20 @@ module CategoryHashtag
           # is no child then the "parent" part of the slug is just the
           # entire slug we look for.
           #
-          # Otherwise if the child slug is present, we find the parent
-          # by its slug then find the child by its slug and its parent's
-          # ID to make sure they match.
+          # Otherwise if the child slug is present, we find the child
+          # by its slug then find the parent by its slug and the child's
+          # parent ID to make sure they match.
           if child_slug.present?
-            parent_category = categories.find { |cat| cat.slug.casecmp?(parent_slug) }
-            if parent_category.present?
-              categories.find do |cat|
-                cat.slug.downcase == child_slug && cat.parent_category_id == parent_category.id
+            categories.find do |cat|
+              if cat.slug.casecmp?(child_slug) && cat.parent_category_id
+                categories.find do |parent_category|
+                  parent_category.id == cat.parent_category_id &&
+                    parent_category.slug.casecmp?(parent_slug)
+                end
               end
             end
           else
-            categories.find { |cat| cat.slug.downcase == parent_slug && cat.top_level? }
+            categories.find { |cat| cat.slug.casecmp?(parent_slug) && cat.top_level? }
           end
         end
         .compact
diff --git a/app/services/category_hashtag_data_source.rb b/app/services/category_hashtag_data_source.rb
index fe8f63caa8e..85403cf5b16 100644
--- a/app/services/category_hashtag_data_source.rb
+++ b/app/services/category_hashtag_data_source.rb
@@ -32,7 +32,11 @@ class CategoryHashtagDataSource
   end
 
   def self.lookup(guardian, slugs)
-    user_categories = Category.secured(guardian).includes(:parent_category)
+    user_categories =
+      Category
+        .secured(guardian)
+        .includes(:parent_category)
+        .order("parent_category_id ASC NULLS FIRST, id ASC")
     Category
       .query_loaded_from_slugs(slugs, user_categories)
       .map { |category| category_to_hashtag_item(category) }
diff --git a/spec/requests/hashtags_controller_spec.rb b/spec/requests/hashtags_controller_spec.rb
index 565e2268d14..968465bd0a0 100644
--- a/spec/requests/hashtags_controller_spec.rb
+++ b/spec/requests/hashtags_controller_spec.rb
@@ -275,6 +275,8 @@ RSpec.describe HashtagsController do
 
             qux = Fabricate(:category_with_definition, slug: "qux")
             quxbar = Fabricate(:category_with_definition, slug: "bar", parent_category_id: qux.id)
+            quxbarbaz =
+              Fabricate(:category_with_definition, slug: "baz", parent_category_id: quxbar.id)
 
             invalid_slugs = [":"]
             child_slugs = %w[bar baz]
diff --git a/spec/services/category_hashtag_data_source_spec.rb b/spec/services/category_hashtag_data_source_spec.rb
index 26098e69f8d..5140855158e 100644
--- a/spec/services/category_hashtag_data_source_spec.rb
+++ b/spec/services/category_hashtag_data_source_spec.rb
@@ -40,6 +40,47 @@ RSpec.describe CategoryHashtagDataSource do
       group.add(user)
       expect(described_class.lookup(Guardian.new(user), ["secret"]).first).not_to eq(nil)
     end
+
+    context "with sub-sub-categories" do
+      before { SiteSetting.max_category_nesting = 3 }
+
+      it "returns the first matching grandchild category (ordered by IDs) when there are multiple categories with the same slug" do
+        parent1 = Fabricate(:category, slug: "parent1")
+        parent2 = Fabricate(:category, slug: "parent2")
+
+        parent1_child = Fabricate(:category, slug: "child", parent_category_id: parent1.id)
+        parent1_child_grandchild =
+          Fabricate(:category, slug: "grandchild", parent_category_id: parent1_child.id)
+
+        parent2_child = Fabricate(:category, slug: "child", parent_category_id: parent2.id)
+        parent2_child_grandchild =
+          Fabricate(:category, slug: "grandchild", parent_category_id: parent2_child.id)
+
+        result = described_class.lookup(guardian, ["child:grandchild"])
+        expect(result.map(&:relative_url)).to eq([parent1_child_grandchild.url])
+
+        parent1_child.destroy
+        parent1_child = Fabricate(:category, slug: "child", parent_category_id: parent1.id)
+
+        result = described_class.lookup(guardian, ["child:grandchild"])
+        expect(result.map(&:relative_url)).to eq([parent2_child_grandchild.url])
+      end
+
+      it "returns the correct grandchild category when there are multiple children with the same slug and only one of them has the correct grandchild" do
+        parent1 = Fabricate(:category, slug: "parent1")
+        parent1_child = Fabricate(:category, slug: "child", parent_category_id: parent1.id)
+        parent1_child_grandchild =
+          Fabricate(:category, slug: "another-grandchild", parent_category_id: parent1_child.id)
+
+        parent2 = Fabricate(:category, slug: "parent2")
+        parent2_child = Fabricate(:category, slug: "child", parent_category_id: parent2.id)
+        parent2_child_grandchild =
+          Fabricate(:category, slug: "grandchild", parent_category_id: parent2_child.id)
+
+        result = described_class.lookup(guardian, ["child:grandchild"])
+        expect(result.map(&:relative_url)).to eq([parent2_child_grandchild.url])
+      end
+    end
   end
 
   describe "#search" do