diff --git a/frappe/templates/generators/web_form.html b/frappe/templates/generators/web_form.html
index 6c8ca1f6de..a7376c2586 100644
--- a/frappe/templates/generators/web_form.html
+++ b/frappe/templates/generators/web_form.html
@@ -332,7 +332,6 @@ frappe.ready(function() {
 			var input = $input.get(0);
 			var reader = new FileReader();
 
-			input.filedata = null;
 			if(input.files.length) {
 				file = input.files[0];
 				frappe.file_reading = true;
@@ -396,9 +395,11 @@ frappe.ready(function() {
 
 	// change attach
 	$form.on("click", ".change-attach", function() {
-		$(this).parent().addClass("hide")
+		var input_wrapper = $(this).parent().addClass("hide")
 			.parent().find(".attach-input-wrap").removeClass("hide");
 
+		input_wrapper.find('input').val('');
+
 		frappe.form_dirty = true;
 
 		return false;
@@ -513,7 +514,12 @@ frappe.ready(function() {
 			var $input = $(this);
 			var input_type = $input.attr("type");
 			if(input_type==="file") {
-				var val = $input.get(0).filedata;
+				// save filedata dict as value
+				if($input.get(0).filedata) {
+					var val = $input.get(0).filedata;
+				} else {
+					var val = {'__no_attachment': 1}
+				}
 			} else if(input_type==="checkbox") {
 				var val = $input.prop("checked") ? 1 : 0;
 			} else if($input.attr("data-fieldtype")==="Date") {
@@ -639,11 +645,11 @@ frappe.ready(function() {
 				dateFormat: frappe.datepicker_format,
 			});
 
-			// convert dates from YYYY-MM-DD to user format
+			// initialize dates from YYYY-MM-DD to user format
 			$dates.each(function() {
-				var val = $(this).val();
+				var val = $(this).attr('value');
 				if(val) {
-					$(this).val(moment(val, 'YYYY-MM-DD').format());
+					$(this).val(moment(val, 'YYYY-MM-DD').format()).trigger('change');
 				}
 			});
 		}
diff --git a/frappe/utils/file_manager.py b/frappe/utils/file_manager.py
index ece60b2e3a..63997aa9da 100644
--- a/frappe/utils/file_manager.py
+++ b/frappe/utils/file_manager.py
@@ -259,6 +259,8 @@ def remove_file(fid, attached_to_doctype=None, attached_to_name=None):
 	if attached_to_doctype and attached_to_name:
 		doc = frappe.get_doc(attached_to_doctype, attached_to_name)
 		ignore_permissions = doc.has_permission("write") or False
+		if frappe.flags.in_web_form:
+			ignore_permissions = True
 		if not file_name:
 			file_name = frappe.db.get_value("File", fid, "file_name")
 		comment = doc.add_comment("Attachment Removed", _("Removed {0}").format(file_name))
diff --git a/frappe/website/doctype/web_form/web_form.py b/frappe/website/doctype/web_form/web_form.py
index 4d28d5ee3e..7c3ab06d2d 100644
--- a/frappe/website/doctype/web_form/web_form.py
+++ b/frappe/website/doctype/web_form/web_form.py
@@ -304,6 +304,7 @@ def get_context(context):
 def accept(web_form, data):
 	data = frappe._dict(json.loads(data))
 	files = []
+	files_to_delete = []
 
 	web_form = frappe.get_doc("Web Form", web_form)
 	if data.doctype != web_form.doc_type:
@@ -312,6 +313,8 @@ def accept(web_form, data):
 	elif data.name and not web_form.allow_edit:
 		frappe.throw(_("You are not allowed to update this Web Form Document"))
 
+	frappe.flags.in_web_form = True
+
 	if data.name:
 		# update
 		doc = frappe.get_doc(data.doctype, data.name)
@@ -326,6 +329,9 @@ def accept(web_form, data):
 				if "__file_attachment" in value:
 					files.append((fieldname, value))
 					continue
+				if '__no_attachment' in value:
+					files_to_delete.append(doc.get(fieldname))
+					value = ''
 
 			except ValueError:
 				pass
@@ -351,7 +357,7 @@ def accept(web_form, data):
 		for f in files:
 			fieldname, filedata = f
 
-			# remove earlier attachmed file (if exists)
+			# remove earlier attached file (if exists)
 			if doc.get(fieldname):
 				remove_file_by_url(doc.get(fieldname), doc.doctype, doc.name)
 
@@ -364,6 +370,11 @@ def accept(web_form, data):
 
 		doc.save()
 
+	if files_to_delete:
+		for f in files_to_delete:
+			if f:
+				remove_file_by_url(f, doc.doctype, doc.name)
+
 	return doc.name
 
 @frappe.whitelist()