diff --git a/app/models/rule/condition_filter.rb b/app/models/rule/condition_filter.rb
index 6fa463a50..ad0574386 100644
--- a/app/models/rule/condition_filter.rb
+++ b/app/models/rule/condition_filter.rb
@@ -72,10 +72,12 @@ class Rule::ConditionFilter
           "#{field} #{sanitize_operator(operator)}"
         )
       else
-        sanitized_value = operator == "like" ? "%#{ActiveRecord::Base.sanitize_sql_like(value)}%" : value
+        normalized_value = normalize_value(value)
+        normalized_field = normalize_field(field)
+        sanitized_value = operator == "like" ? "%#{ActiveRecord::Base.sanitize_sql_like(normalized_value)}%" : normalized_value
 
         ActiveRecord::Base.sanitize_sql_for_conditions([
-          "#{field} #{sanitize_operator(operator)} ?",
+          "#{normalized_field} #{sanitize_operator(operator)} ?",
           sanitized_value
         ])
       end
@@ -93,4 +95,16 @@ class Rule::ConditionFilter
         operator
       end
     end
+
+    def normalize_value(value)
+      return value unless type == "text"
+
+      value.to_s.gsub(/\s+/, " ").strip
+    end
+
+    def normalize_field(field)
+      return field unless type == "text"
+
+      "BTRIM(REGEXP_REPLACE(#{field}, '[[:space:]]+', ' ', 'g'))"
+    end
 end
diff --git a/test/models/rule_test.rb b/test/models/rule_test.rb
index 731199fab..408cb8cca 100644
--- a/test/models/rule_test.rb
+++ b/test/models/rule_test.rb
@@ -94,6 +94,30 @@ class RuleTest < ActiveSupport::TestCase
     assert_not transaction_entry.excluded, "Transaction should not be excluded when attribute is locked"
   end
 
+  test "transaction name rules normalize whitespace in comparisons" do
+    transaction_entry = create_transaction(
+      date: Date.current,
+      account: @account,
+      name: "Company  -   Mobile",
+      amount: 80
+    )
+
+    rule = Rule.create!(
+      family: @family,
+      resource_type: "transaction",
+      effective_date: 1.day.ago.to_date,
+      conditions: [ Rule::Condition.new(condition_type: "transaction_name", operator: "like", value: "Company - Mobile") ],
+      actions: [ Rule::Action.new(action_type: "set_transaction_category", value: @groceries_category.id) ]
+    )
+
+    assert_equal 1, rule.affected_resource_count
+
+    rule.apply
+    transaction_entry.reload
+
+    assert_equal @groceries_category, transaction_entry.transaction.category
+  end
+
   # Artificial limitation put in place to prevent users from creating overly complex rules
   # Rules should be shallow and wide
   test "no nested compound conditions" do