diff --git a/.grit/patterns/python/_test_correct_source.md b/.grit/patterns/python/_test_correct_source.md
new file mode 100644
index 00000000..28c46423
--- /dev/null
+++ b/.grit/patterns/python/_test_correct_source.md
@@ -0,0 +1,28 @@
+Test for ensuring new imports go to the right place, from [this issue](https://github.com/getgrit/gritql/issues/449).
+
+```grit
+engine marzano(0.1)
+language python
+
+`$x = 1` where {
+    add_import(source="typing_extensions", name="Self"),
+    add_import(source="pydantic", name="model_validator"),
+}
+```
+
+Input:
+
+```python
+import math
+x = 1
+```
+
+Expected output:
+
+```python
+import math
+from typing_extensions import Self
+from pydantic import model_validator
+
+x = 1
+```
diff --git a/.grit/patterns/python/_test_two_imports.md b/.grit/patterns/python/_test_two_imports.md
new file mode 100644
index 00000000..bd3a57a8
--- /dev/null
+++ b/.grit/patterns/python/_test_two_imports.md
@@ -0,0 +1,27 @@
+Test for adding multiple imports to the same library, for [this issue](https://github.com/getgrit/gritql/issues/450).
+
+```grit
+engine marzano(0.1)
+language python
+
+`x = 1` as $SELF where {
+    add_import(source="pydantic", name="Self"),
+    add_import(source="pydantic", name="pydantic1"),
+}
+```
+
+Input:
+
+```python
+from pydantic import BaseModel, Extra, Field, root_validator
+
+x = 1
+```
+
+Expected Output:
+
+```python
+from pydantic import BaseModel, Extra, Field, root_validator, Self, pydantic1
+
+x = 1
+```
diff --git a/.grit/patterns/python/py_imports.grit b/.grit/patterns/python/py_imports.grit
index d82252f0..b07b857f 100644
--- a/.grit/patterns/python/py_imports.grit
+++ b/.grit/patterns/python/py_imports.grit
@@ -9,8 +9,7 @@ pattern import_from($source, $names) {
 pattern before_each_file_prep_imports() {
     $_ where {
         $GLOBAL_NEW_BARE_IMPORT_NAMES = [],
-        $GLOBAL_NEW_FROM_IMPORT_SOURCES = [],
-        $GLOBAL_NEW_FROM_IMPORT_NAMES = [],
+        $GLOBAL_NEW_FROM_IMPORTS = [],
         $GLOBAL_IMPORTS_TO_REMOVE = [],
     }
 }
@@ -22,26 +21,7 @@ pattern after_each_file_handle_imports() {
   }
 }
 
-pattern process_one_source($p, $all_imports) {
-    [$p, $source] where {
-        $new_names = [],
-        $GLOBAL_NEW_FROM_IMPORT_NAMES <: some bubble($new_names) [$p, $name, $source] where {
-            $new_names += $name,
-        },
-        if ($p <: module(statements = some import_from($source, $names))) {
-            $names_to_add = "",
-            $new_names <: some $name where {
-                if (!$names <: some $name) {
-                    $names_to_add += `, $name`
-                }
-            },
-            $names => `$names$names_to_add`,
-        } else {
-            $joined_names = join(list = $new_names, separator = ", "),
-            $all_imports += `from $source import $joined_names\n`,
-        }
-    }
-}
+
 
 // TODO: remove imports from the global list as we remove them
 pattern handle_one_removal_candidate() {
@@ -93,10 +73,39 @@ predicate remove_import($source) {
   }
 }
 
+pattern process_one_source($all_imports) {
+    $source where {
+        $maybe_new_names = [],
+        $GLOBAL_NEW_FROM_IMPORTS <: some bubble($maybe_new_names, $source) [$candidate_source, $name] where {
+            if ($source <: $candidate_source) {
+                $maybe_new_names += $name
+            }
+        },
+        $new_names = distinct(list=$maybe_new_names),
+        if ($program <: module(statements = some import_from($source, $names))) {
+            $names_to_add = "",
+            $new_names <: some bubble($names_to_add, $names) $new_name where {
+              $names <: not some $new_name,
+              $names_to_add += `, $new_name`
+            },
+            $names => `$names$names_to_add`,
+        } else {
+            $joined_names = join(list = $new_names, separator = ", "),
+            $all_imports += `from $source import $joined_names\n`,
+        }
+    }
+}
+
 pattern insert_imports() {
     $body where {
         $all_imports = "",
-        $GLOBAL_NEW_FROM_IMPORT_SOURCES <: maybe some process_one_source($p, $all_imports),
+        $sources = [],
+        // First make sure we have an enty for each import
+        $GLOBAL_NEW_FROM_IMPORTS <: maybe some bubble($sources) [$source, $name] where {
+          $sources += $source
+        },
+        $unique_sources = distinct(list=$sources),
+        $unique_sources <: maybe some process_one_source($all_imports),
         $GLOBAL_NEW_BARE_IMPORT_NAMES <: maybe some bubble($all_imports) $name where {
             $all_imports += `import $name\n`,
         },
@@ -131,12 +140,7 @@ pattern imported_from($source) {
 pattern ensure_import_from($source) {
     $name where {
         if ($name <: not imported_from($source)) {
-            if ($GLOBAL_NEW_FROM_IMPORT_SOURCES <: not some [$program, $source]) {
-                $GLOBAL_NEW_FROM_IMPORT_SOURCES += [$program, $source]
-            },
-            if ($GLOBAL_NEW_FROM_IMPORT_NAMES <: not some [$program, $name, $source]) {
-                $GLOBAL_NEW_FROM_IMPORT_NAMES += [$program, $name, $source]
-            }
+          $GLOBAL_NEW_FROM_IMPORTS += [$source, $name]
         }
     }
 }