diff --git a/examples/small.properties b/examples/small.properties
index fbb6df9f..627bee97 100644
--- a/examples/small.properties
+++ b/examples/small.properties
@@ -1,2 +1,6 @@
 # great huh
-this.is = a properties file
\ No newline at end of file
+
+# things and stuff
+this.is = a properties file
+# another thing
+this.another = a properties file
diff --git a/pkg/yqlib/decoder_properties.go b/pkg/yqlib/decoder_properties.go
index ae1b04e4..e6aa3288 100644
--- a/pkg/yqlib/decoder_properties.go
+++ b/pkg/yqlib/decoder_properties.go
@@ -51,11 +51,13 @@ func (dec *propertiesDecoder) applyProperty(properties *properties.Properties, c
 	value, _ := properties.Get(key)
 	path := parsePropKey(key)
 
+	log.Debug("comments: %v", properties.GetComments(key))
+	log.Debug("comment: %v", properties.GetComment(key))
 	rhsNode := &yaml.Node{
 		Value:       value,
 		Tag:         "!!str",
 		Kind:        yaml.ScalarNode,
-		LineComment: dec.processComment(properties.GetComment(key)),
+		LineComment: dec.processComment(strings.Join(properties.GetComments(key), "\n")),
 	}
 
 	rhsNode.Tag = guessTagFromCustomType(rhsNode)
diff --git a/pkg/yqlib/doc/operators/load.md b/pkg/yqlib/doc/operators/load.md
index 79dc0149..ff76f442 100644
--- a/pkg/yqlib/doc/operators/load.md
+++ b/pkg/yqlib/doc/operators/load.md
@@ -154,7 +154,9 @@ will output
 cool: things
 more_stuff:
   this:
-    is: a properties file
+    is: a properties file # great huh
+    # things and stuff
+    another: a properties file # another thing
 ```
 
 ## Merge from properties
@@ -173,8 +175,10 @@ yq '. *= load_props("../../examples/small.properties")' sample.yml
 will output
 ```yaml
 this:
-  is: a properties file
+  is: a properties file # great huh
+  # things and stuff
   cool: ay
+  another: a properties file # another thing
 ```
 
 ## Load from base64 encoded file
diff --git a/pkg/yqlib/doc/usage/properties.md b/pkg/yqlib/doc/usage/properties.md
index e676ca1c..d9331aa8 100644
--- a/pkg/yqlib/doc/usage/properties.md
+++ b/pkg/yqlib/doc/usage/properties.md
@@ -139,7 +139,8 @@ yq -p=props sample.properties
 will output
 ```yaml
 person:
-    name: Mike Wazowski # comments on values appear
+    name: Mike Wazowski # block comments come through
+    # comments on values appear
     pets:
         - cat # comments on array values appear
     food:
@@ -164,6 +165,7 @@ yq -p=props -o=props '.person.pets.0 = "dog"' sample.properties
 ```
 will output
 ```properties
+# block comments come through
 # comments on values appear
 person.name = Mike Wazowski
 
diff --git a/pkg/yqlib/encoder_properties.go b/pkg/yqlib/encoder_properties.go
index 745f1279..6b922fd9 100644
--- a/pkg/yqlib/encoder_properties.go
+++ b/pkg/yqlib/encoder_properties.go
@@ -75,7 +75,7 @@ func (pe *propertiesEncoder) Encode(writer io.Writer, node *yaml.Node) error {
 }
 
 func (pe *propertiesEncoder) doEncode(p *properties.Properties, node *yaml.Node, path string) error {
-	p.SetComment(path, headAndLineComment(node))
+	p.SetComment(path, strings.ReplaceAll(headAndLineComment(node), "\n", "\n# "))
 	switch node.Kind {
 	case yaml.ScalarNode:
 		var nodeValue string
diff --git a/pkg/yqlib/properties_test.go b/pkg/yqlib/properties_test.go
index b539270f..1bdaa457 100644
--- a/pkg/yqlib/properties_test.go
+++ b/pkg/yqlib/properties_test.go
@@ -36,7 +36,8 @@ person.pets.0 = cat
 person.food.0 = pizza
 `
 
-const expectedUpdatedProperties = `# comments on values appear
+const expectedUpdatedProperties = `# block comments come through
+# comments on values appear
 person.name = Mike Wazowski
 
 # comments on array values appear