diff --git a/models/issues/issue.go b/models/issues/issue.go
index f04a4ad5c7..f7379b7e0c 100644
--- a/models/issues/issue.go
+++ b/models/issues/issue.go
@@ -153,8 +153,8 @@ type Issue struct {
 }
 
 var (
-	issueTasksPat     = regexp.MustCompile(`(^\s*[-*]\s\[[\sxX]\]\s.)|(\n\s*[-*]\s\[[\sxX]\]\s.)`)
-	issueTasksDonePat = regexp.MustCompile(`(^\s*[-*]\s\[[xX]\]\s.)|(\n\s*[-*]\s\[[xX]\]\s.)`)
+	issueTasksPat     = regexp.MustCompile(`(^|\n)\s*[-*]\s*\[[\sxX]\]`)
+	issueTasksDonePat = regexp.MustCompile(`(^|\n)\s*[-*]\s*\[[xX]\]`)
 )
 
 // IssueIndex represents the issue index table
diff --git a/tests/integration/issue_test.go b/tests/integration/issue_test.go
index ccae0b00ea..bf05c3c0a6 100644
--- a/tests/integration/issue_test.go
+++ b/tests/integration/issue_test.go
@@ -10,6 +10,7 @@ import (
 	"net/http"
 	"net/url"
 	"path"
+	"regexp"
 	"strconv"
 	"strings"
 	"testing"
@@ -236,9 +237,13 @@ func testNewIssue(t *testing.T, session *TestSession, user, repo, title, content
 	htmlDoc = NewHTMLParser(t, resp.Body)
 	val := htmlDoc.doc.Find("#issue-title-display").Text()
 	assert.Contains(t, val, title)
-	val = htmlDoc.doc.Find(".comment .render-content p").First().Text()
-	assert.Equal(t, content, val)
-
+	// test for first line only and if it contains only letters and spaces
+	contentFirstLine := strings.Split(content, "\n")[0]
+	patNotLetterOrSpace := regexp.MustCompile(`[^\p{L}\s]`)
+	if len(contentFirstLine) != 0 && !patNotLetterOrSpace.MatchString(contentFirstLine) {
+		val = htmlDoc.doc.Find(".comment .render-content p").First().Text()
+		assert.Equal(t, contentFirstLine, val)
+	}
 	return issueURL
 }
 
@@ -281,6 +286,50 @@ func TestNewIssue(t *testing.T) {
 	testNewIssue(t, session, "user2", "repo1", "Title", "Description")
 }
 
+func TestIssueCheckboxes(t *testing.T) {
+	defer tests.PrepareTestEnv(t)()
+	session := loginUser(t, "user2")
+	issueURL := testNewIssue(t, session, "user2", "repo1", "Title", `- [x] small x
+- [X] capital X
+- [ ] empty
+  - [x]x without gap
+  - [ ]empty without gap
+- [x]
+x on new line
+- [ ]
+empty on new line
+	-	[	]	tabs instead of spaces
+Description`)
+	req := NewRequest(t, "GET", issueURL)
+	resp := session.MakeRequest(t, req, http.StatusOK)
+	issueContent := NewHTMLParser(t, resp.Body).doc.Find(".comment .render-content").First()
+	isCheckBox := func(i int, s *goquery.Selection) bool {
+		typeVal, typeExists := s.Attr("type")
+		return typeExists && typeVal == "checkbox"
+	}
+	isChecked := func(i int, s *goquery.Selection) bool {
+		_, checkedExists := s.Attr("checked")
+		return checkedExists
+	}
+	checkBoxes := issueContent.Find("input").FilterFunction(isCheckBox)
+	assert.Equal(t, 8, checkBoxes.Length())
+	assert.Equal(t, 4, checkBoxes.FilterFunction(isChecked).Length())
+
+	// Issues list should show the correct numbers of checked and total checkboxes
+	repo, err := repo_model.GetRepositoryByOwnerAndName(db.DefaultContext, "user2", "repo1")
+	assert.NoError(t, err)
+	req = NewRequestf(t, "GET", "%s/issues", repo.Link())
+	resp = MakeRequest(t, req, http.StatusOK)
+
+	htmlDoc := NewHTMLParser(t, resp.Body)
+	issuesSelection := htmlDoc.Find("#issue-list .flex-item")
+	assert.Equal(t, "4 / 8", strings.TrimSpace(issuesSelection.Find(".checklist").Text()))
+	value, _ := issuesSelection.Find("progress").Attr("value")
+	vmax, _ := issuesSelection.Find("progress").Attr("max")
+	assert.Equal(t, "4", value)
+	assert.Equal(t, "8", vmax)
+}
+
 func TestIssueDependencies(t *testing.T) {
 	defer tests.PrepareTestEnv(t)()
 
diff --git a/web_src/js/markup/tasklist.js b/web_src/js/markup/tasklist.js
index a40b5e4abd..375810dc2f 100644
--- a/web_src/js/markup/tasklist.js
+++ b/web_src/js/markup/tasklist.js
@@ -32,11 +32,11 @@ export function initMarkupTasklist() {
         const buffer = encoder.encode(oldContent);
         // Indexes may fall off the ends and return undefined.
         if (buffer[position - 1] !== '['.codePointAt(0) ||
-          buffer[position] !== ' '.codePointAt(0) && buffer[position] !== 'x'.codePointAt(0) ||
+          buffer[position] !== ' '.codePointAt(0) && buffer[position] !== 'x'.codePointAt(0) && buffer[position] !== 'X'.codePointAt(0) ||
           buffer[position + 1] !== ']'.codePointAt(0)) {
           // Position is probably wrong.  Revert and don't allow change.
           checkbox.checked = !checkbox.checked;
-          throw new Error(`Expected position to be space or x and surrounded by brackets, but it's not: position=${position}`);
+          throw new Error(`Expected position to be space, x or X and surrounded by brackets, but it's not: position=${position}`);
         }
         buffer.set(encoder.encode(checkboxCharacter), position);
         const newContent = new TextDecoder().decode(buffer);