diff --git a/app/models/rule_import.rb b/app/models/rule_import.rb
index bae5820d7..48ae775fc 100644
--- a/app/models/rule_import.rb
+++ b/app/models/rule_import.rb
@@ -289,9 +289,14 @@ class RuleImport < Import
     def parse_json_safely(json_string, field_name)
       return [] if json_string.blank?
 
-      # Clean up the JSON string - remove extra escaping that might come from CSV parsing
       cleaned = json_string.to_s.strip
 
+      # Most API-created rows already store valid JSON. Parse them as-is before
+      # falling back to the legacy cleanup path for older malformed payloads.
+      parse_json_payload(cleaned, normalize_legacy_strings: false)
+    rescue JSON::ParserError
+      # Clean up the JSON string - remove extra escaping that might come from CSV parsing
+
       # Remove surrounding quotes if present (both single and double)
       cleaned = cleaned.gsub(/\A["']+|["']+\z/, "")
 
@@ -321,8 +326,46 @@ class RuleImport < Import
       end
 
       # Try parsing
-      JSON.parse(cleaned)
+      parse_json_payload(cleaned, normalize_legacy_strings: true)
     rescue JSON::ParserError => e
       raise JSON::ParserError.new("Invalid JSON in #{field_name}: #{e.message}. Raw value: #{json_string.inspect}")
     end
+
+    def parse_json_payload(payload, normalize_legacy_strings:)
+      parsed = JSON.parse(payload)
+      parsed = JSON.parse(parsed) if wrapped_json_payload?(parsed)
+
+      normalize_json_values(parsed, normalize_legacy_strings:)
+    end
+
+    def wrapped_json_payload?(value)
+      return false unless value.is_a?(String)
+
+      stripped_value = value.strip
+      stripped_value.start_with?("[", "{")
+    end
+
+    def normalize_json_values(value, normalize_legacy_strings:)
+      case value
+      when Array
+        value.map { |item| normalize_json_values(item, normalize_legacy_strings:) }
+      when Hash
+        value.transform_values { |item| normalize_json_values(item, normalize_legacy_strings:) }
+      when String
+        normalized = value
+          .gsub(/\\u([0-9a-fA-F]{4})/i) { [ $1.to_i(16) ].pack("U") }
+          .gsub('\\"', '"')
+
+        if normalize_legacy_strings
+          normalized = normalized
+            .gsub("\\n", "\n")
+            .gsub("\\r", "\r")
+            .gsub("\\t", "\t")
+        end
+
+        normalized
+      else
+        value
+      end
+    end
 end
diff --git a/test/models/rule_import_test.rb b/test/models/rule_import_test.rb
index 23cc246f8..ca95f8390 100644
--- a/test/models/rule_import_test.rb
+++ b/test/models/rule_import_test.rb
@@ -233,4 +233,83 @@ class RuleImportTest < ActiveSupport::TestCase
       import.send(:import!)
     end
   end
+
+  test "imports valid JSON conditions whose values contain escaped quotes" do
+    csv = CSV.generate do |out|
+      out << %w[name resource_type active effective_date conditions actions]
+      out << [
+        "Quoted value rule",
+        "transaction",
+        true,
+        "",
+        [ { condition_type: "transaction_name", operator: "=", value: "ני\\u0022ע-קניה" } ].to_json,
+        [ { action_type: "set_transaction_name", value: "Quoted transfer" } ].to_json
+      ]
+    end
+
+    import = @family.imports.create!(type: "RuleImport", raw_file_str: csv, col_sep: ",")
+    import.generate_rows_from_csv
+
+    assert_nothing_raised do
+      import.send(:import!)
+    end
+
+    rule = Rule.find_by!(family: @family, name: "Quoted value rule")
+    condition = rule.conditions.first
+    assert_equal "ני\"ע-קניה", condition.value
+  end
+
+  test "imports wrapped JSON payloads from legacy rows" do
+    wrapped_conditions = [ { condition_type: "transaction_name", operator: "like", value: "legacy grocery" } ].to_json.to_json
+    wrapped_actions = [ { action_type: "set_transaction_category", value: "Groceries" } ].to_json.to_json
+
+    csv = CSV.generate do |out|
+      out << %w[name resource_type active effective_date conditions actions]
+      out << [
+        "Wrapped payload rule",
+        "transaction",
+        true,
+        "",
+        wrapped_conditions,
+        wrapped_actions
+      ]
+    end
+
+    import = @family.imports.create!(type: "RuleImport", raw_file_str: csv, col_sep: ",")
+    import.generate_rows_from_csv
+
+    assert_nothing_raised do
+      import.send(:import!)
+    end
+
+    rule = Rule.find_by!(family: @family, name: "Wrapped payload rule")
+    condition = rule.conditions.first
+    action = rule.actions.first
+
+    assert_equal "legacy grocery", condition.value
+    assert_equal @category.id, action.value
+  end
+
+  test "preserves literal backslash sequences in valid JSON values" do
+    csv = CSV.generate do |out|
+      out << %w[name resource_type active effective_date conditions actions]
+      out << [
+        "Literal backslash rule",
+        "transaction",
+        true,
+        "",
+        [ { condition_type: "transaction_name", operator: "=", value: 'C:\new\test' } ].to_json,
+        [ { action_type: "set_transaction_name", value: "Path rule" } ].to_json
+      ]
+    end
+
+    import = @family.imports.create!(type: "RuleImport", raw_file_str: csv, col_sep: ",")
+    import.generate_rows_from_csv
+    import.send(:import!)
+
+    rule = Rule.find_by!(family: @family, name: "Literal backslash rule")
+    condition = rule.conditions.first
+
+    assert_equal 'C:\new\test', condition.value
+  end
 end