diff --git a/routers/web/repo/issue.go b/routers/web/repo/issue.go
index 9639ea820..3162e0932 100644
--- a/routers/web/repo/issue.go
+++ b/routers/web/repo/issue.go
@@ -1728,10 +1728,12 @@ func UpdateIssueContent(ctx *context.Context) {
 		return
 	}
 
-	files := ctx.QueryStrings("files[]")
-	if err := updateAttachments(issue, files); err != nil {
-		ctx.ServerError("UpdateAttachments", err)
-		return
+	// when update the request doesn't intend to update attachments (eg: change checkbox state), ignore attachment updates
+	if !ctx.QueryBool("ignore_attachments") {
+		if err := updateAttachments(issue, ctx.QueryStrings("files[]")); err != nil {
+			ctx.ServerError("UpdateAttachments", err)
+			return
+		}
 	}
 
 	content, err := markdown.RenderString(&markup.RenderContext{
@@ -2128,13 +2130,6 @@ func UpdateCommentContent(ctx *context.Context) {
 		return
 	}
 
-	if comment.Type == models.CommentTypeComment {
-		if err := comment.LoadAttachments(); err != nil {
-			ctx.ServerError("LoadAttachments", err)
-			return
-		}
-	}
-
 	if !ctx.IsSigned || (ctx.User.ID != comment.PosterID && !ctx.Repo.CanWriteIssuesOrPulls(comment.Issue.IsPull)) {
 		ctx.Error(http.StatusForbidden)
 		return
@@ -2156,10 +2151,19 @@ func UpdateCommentContent(ctx *context.Context) {
 		return
 	}
 
-	files := ctx.QueryStrings("files[]")
-	if err := updateAttachments(comment, files); err != nil {
-		ctx.ServerError("UpdateAttachments", err)
-		return
+	if comment.Type == models.CommentTypeComment {
+		if err := comment.LoadAttachments(); err != nil {
+			ctx.ServerError("LoadAttachments", err)
+			return
+		}
+	}
+
+	// when the update request doesn't intend to update attachments (eg: change checkbox state), ignore attachment updates
+	if !ctx.QueryBool("ignore_attachments") {
+		if err := updateAttachments(comment, ctx.QueryStrings("files[]")); err != nil {
+			ctx.ServerError("UpdateAttachments", err)
+			return
+		}
 	}
 
 	content, err := markdown.RenderString(&markup.RenderContext{
diff --git a/web_src/js/markup/tasklist.js b/web_src/js/markup/tasklist.js
index 24b29ddb7..ea1a1f824 100644
--- a/web_src/js/markup/tasklist.js
+++ b/web_src/js/markup/tasklist.js
@@ -46,9 +46,10 @@ export function initMarkupTasklist() {
           const {updateUrl, context} = editContentZone.dataset;
 
           await $.post(updateUrl, {
+            ignore_attachments: true,
             _csrf: window.config.csrf,
             content: newContent,
-            context,
+            context
           });
 
           rawContent.textContent = newContent;