diff --git a/loader/loader.go b/loader/loader.go
index 035c8810..eece6798 100644
--- a/loader/loader.go
+++ b/loader/loader.go
@@ -509,7 +509,7 @@ func loadYamlFile(ctx context.Context,
 				break
 			}
 			if err != nil {
-				return nil, nil, err
+				return nil, nil, fmt.Errorf("failed to parse %s: %w", file.Filename, err)
 			}
 			processor = reset
 			if err := processRawYaml(raw, processor); err != nil {
diff --git a/loader/loader_test.go b/loader/loader_test.go
index ee66e8b0..719f5cab 100644
--- a/loader/loader_test.go
+++ b/loader/loader_test.go
@@ -991,7 +991,7 @@ func TestDecodeErrors(t *testing.T) {
 
 	configDetails := buildConfigDetails(dict, nil)
 	_, err := LoadWithContext(context.TODO(), configDetails)
-	assert.Error(t, err, "yaml: line 4: found a tab character that violates indentation")
+	assert.Error(t, err, "failed to parse filename0.yml: yaml: line 4: found a tab character that violates indentation")
 }
 
 func TestBuildProperties(t *testing.T) {
diff --git a/loader/merge_reset_test.go b/loader/merge_reset_test.go
index f6045b3b..fcb2aaaf 100644
--- a/loader/merge_reset_test.go
+++ b/loader/merge_reset_test.go
@@ -79,5 +79,5 @@ func Test_DuplicateReset(t *testing.T) {
 	}, func(options *Options) {
 		options.SkipNormalization = true
 	})
-	assert.Error(t, err, "line 6: mapping key \"command\" already defined at line 5")
+	assert.Error(t, err, "failed to parse duplicate.yml: line 6: mapping key \"command\" already defined at line 5")
 }
diff --git a/loader/reset_test.go b/loader/reset_test.go
index 3814b01a..2c51dee3 100644
--- a/loader/reset_test.go
+++ b/loader/reset_test.go
@@ -163,7 +163,7 @@ x-healthcheck: &healthcheck
     <<: *healthcheck
 `,
 			expectError: true,
-			errorMsg:    "cycle detected: node at path x-healthcheck.egress-service.egress-service references node at path x-healthcheck.egress-service",
+			errorMsg:    "failed to parse (inline): cycle detected: node at path x-healthcheck.egress-service.egress-service references node at path x-healthcheck.egress-service",
 		},
 	}