diff --git a/services/search/pkg/parity/query_mediatype_test.go b/services/search/pkg/parity/query_mediatype_test.go
index cd43ff89d5..32a79a89fa 100644
--- a/services/search/pkg/parity/query_mediatype_test.go
+++ b/services/search/pkg/parity/query_mediatype_test.go
@@ -20,6 +20,10 @@ func mediatypeGroup() queryGroup {
 			{id: 4, query: `mediatype:*jpeg`, want: []string{"photo.jpg"}},
 			{id: 5, query: `mediatype:image`, want: []string{"photo.jpg"}},
 			{id: 6, query: `mediatype:folder`, want: []string{"albums", "drafts"}},
+			{id: 7, query: `mediatype:file`, want: []string{"notes.md", "photo.jpg"}},
+			{id: 8, query: `NOT mediatype:file`, want: []string{"albums", "drafts"}},
+			{id: 9, query: `mediatype:file OR mediatype:image`, want: []string{"notes.md", "photo.jpg"}},
+			{id: 10, query: `NOT mediatype:(image OR folder)`, want: []string{"notes.md"}},
 		},
 	}
 }
diff --git a/services/search/pkg/query/bleve/compiler.go b/services/search/pkg/query/bleve/compiler.go
index e4be2d50c9..1ca00dbe7e 100644
--- a/services/search/pkg/query/bleve/compiler.go
+++ b/services/search/pkg/query/bleve/compiler.go
@@ -269,10 +269,7 @@ func walk(offset int, nodes []ast.Node) (bleveQuery.Query, int, error) {
 
 func nextNode(offset int, nodes []ast.Node) (bleveQuery.Query, int, error) {
 	if n, ok := nodes[offset].(*ast.GroupNode); ok {
-		if n.Key != "" {
-			n = normalizeGroupingProperty(n)
-		}
-
+		// keys are resolved and group keys propagated by normalize
 		gq, _, err := walk(0, n.Nodes)
 		if err != nil {
 			return nil, 0, err
@@ -359,12 +356,3 @@ func numberRange(field string, operator *ast.OperatorNode, value float64) bleveQ
 
 	return q
 }
-
-func normalizeGroupingProperty(group *ast.GroupNode) *ast.GroupNode {
-	for _, n := range group.Nodes {
-		if onode, ok := n.(*ast.StringNode); ok {
-			onode.Key = group.Key
-		}
-	}
-	return group
-}
diff --git a/services/search/pkg/query/mimetype/mimetype.go b/services/search/pkg/query/mimetype/mimetype.go
index ca61e651ac..64b901beb5 100644
--- a/services/search/pkg/query/mimetype/mimetype.go
+++ b/services/search/pkg/query/mimetype/mimetype.go
@@ -23,9 +23,13 @@ func Expand(key, value string) []ast.Node {
 	value = strings.ToLower(value)
 	switch value {
 	case "file":
+		// grouped so the negation stays atomic when it composes with other
+		// terms (mediatype:file OR ...)
 		return []ast.Node{
-			&ast.OperatorNode{Value: kql.BoolNOT},
-			&ast.StringNode{Key: field, Value: "httpd/unix-directory"},
+			&ast.GroupNode{Nodes: []ast.Node{
+				&ast.OperatorNode{Value: kql.BoolNOT},
+				&ast.StringNode{Key: field, Value: "httpd/unix-directory"},
+			}},
 		}
 	case "folder":
 		return term("httpd/unix-directory")
diff --git a/services/search/pkg/query/mimetype/mimetype_test.go b/services/search/pkg/query/mimetype/mimetype_test.go
index d48fb44e6a..b21c5befbe 100644
--- a/services/search/pkg/query/mimetype/mimetype_test.go
+++ b/services/search/pkg/query/mimetype/mimetype_test.go
@@ -56,8 +56,10 @@ var _ = Describe("Expand", func() {
 
 	It("expands file to not-a-folder", func() {
 		Expect(mimetype.Expand("mediatype", "file")).To(Equal([]ast.Node{
-			&ast.OperatorNode{Value: "NOT"},
-			&ast.StringNode{Key: "MimeType", Value: "httpd/unix-directory"},
+			&ast.GroupNode{Nodes: []ast.Node{
+				&ast.OperatorNode{Value: "NOT"},
+				&ast.StringNode{Key: "MimeType", Value: "httpd/unix-directory"},
+			}},
 		}))
 	})
 
diff --git a/services/search/pkg/query/normalize_test.go b/services/search/pkg/query/normalize_test.go
index 5260eae383..cb77be7c12 100644
--- a/services/search/pkg/query/normalize_test.go
+++ b/services/search/pkg/query/normalize_test.go
@@ -73,8 +73,10 @@ var _ = Describe("Normalize", func() {
 			&ast.OperatorNode{Value: "AND"},
 			&ast.StringNode{Key: "photo.cameraMake", Value: "canon", CaseInsensitive: true},
 			&ast.OperatorNode{Value: "AND"},
-			&ast.OperatorNode{Value: "NOT"},
-			&ast.StringNode{Key: "MimeType", Value: "httpd/unix-directory"},
+			&ast.GroupNode{Nodes: []ast.Node{
+				&ast.OperatorNode{Value: "NOT"},
+				&ast.StringNode{Key: "MimeType", Value: "httpd/unix-directory"},
+			}},
 			&ast.OperatorNode{Value: "AND"},
 			&ast.NumberNode{Key: "Size", Value: 100},
 		}))