diff --git a/pkg/channels/telegram.go b/pkg/channels/telegram.go
index 3ad4818c3..a18fd1ed8 100644
--- a/pkg/channels/telegram.go
+++ b/pkg/channels/telegram.go
@@ -418,9 +418,9 @@ func markdownToTelegramHTML(text string) string {
 	inlineCodes := extractInlineCodes(text)
 	text = inlineCodes.text
 
-	text = regexp.MustCompile(`^#{1,6}\s+(.+)$`).ReplaceAllString(text, "$1")
+	text = regexp.MustCompile(`(?m)^#{1,6}\s+(.+)$`).ReplaceAllString(text, "$1")
 
-	text = regexp.MustCompile(`^>\s*(.*)$`).ReplaceAllString(text, "$1")
+	text = regexp.MustCompile(`(?m)^>\s*(.*)$`).ReplaceAllString(text, "$1")
 
 	text = escapeHTML(text)
 
@@ -441,7 +441,9 @@ func markdownToTelegramHTML(text string) string {
 
 	text = regexp.MustCompile(`~~(.+?)~~`).ReplaceAllString(text, "<s>$1</s>")
 
-	text = regexp.MustCompile(`^[-*]\s+`).ReplaceAllString(text, "• ")
+	text = regexp.MustCompile(`(?m)^[-*]\s+`).ReplaceAllString(text, "• ")
+
+	text = regexp.MustCompile(`(?m)^\d+\.\s+`).ReplaceAllString(text, "• ")
 
 	for i, code := range inlineCodes.codes {
 		escaped := escapeHTML(code)
@@ -470,8 +472,11 @@ func extractCodeBlocks(text string) codeBlockMatch {
 		codes = append(codes, match[1])
 	}
 
+	idx := 0
 	text = re.ReplaceAllStringFunc(text, func(m string) string {
-		return fmt.Sprintf("\x00CB%d\x00", len(codes)-1)
+		placeholder := fmt.Sprintf("\x00CB%d\x00", idx)
+		idx++
+		return placeholder
 	})
 
 	return codeBlockMatch{text: text, codes: codes}
@@ -491,8 +496,11 @@ func extractInlineCodes(text string) inlineCodeMatch {
 		codes = append(codes, match[1])
 	}
 
+	idx := 0
 	text = re.ReplaceAllStringFunc(text, func(m string) string {
-		return fmt.Sprintf("\x00IC%d\x00", len(codes)-1)
+		placeholder := fmt.Sprintf("\x00IC%d\x00", idx)
+		idx++
+		return placeholder
 	})
 
 	return inlineCodeMatch{text: text, codes: codes}
diff --git a/pkg/channels/telegram_test.go b/pkg/channels/telegram_test.go
new file mode 100644
index 000000000..158e56496
--- /dev/null
+++ b/pkg/channels/telegram_test.go
@@ -0,0 +1,45 @@
+package channels
+
+import (
+	"strings"
+	"testing"
+)
+
+func TestMarkdownToTelegramHTML_MultilineFormatting(t *testing.T) {
+	input := "## Titulo\n- item um\n- item dois\n1. item tres\n> citação"
+	got := markdownToTelegramHTML(input)
+
+	if strings.Contains(got, "##") {
+		t.Fatalf("heading marker should be removed, got: %q", got)
+	}
+	if !strings.Contains(got, "• item um") || !strings.Contains(got, "• item dois") || !strings.Contains(got, "• item tres") {
+		t.Fatalf("list markers should be normalized, got: %q", got)
+	}
+	if strings.Contains(got, "> citação") {
+		t.Fatalf("blockquote marker should be removed, got: %q", got)
+	}
+}
+
+func TestMarkdownToTelegramHTML_MultipleCodeBlocks(t *testing.T) {
+	input := "```go\nfmt.Println(1)\n```\ntexto\n```js\nconsole.log(2)\n```"
+	got := markdownToTelegramHTML(input)
+
+	if strings.Count(got, "<pre><code>") != 2 {
+		t.Fatalf("expected 2 code blocks, got: %q", got)
+	}
+	if !strings.Contains(got, "fmt.Println(1)") || !strings.Contains(got, "console.log(2)") {
+		t.Fatalf("missing code block contents, got: %q", got)
+	}
+}
+
+func TestMarkdownToTelegramHTML_MultipleInlineCodes(t *testing.T) {
+	input := "use `foo` and `bar`"
+	got := markdownToTelegramHTML(input)
+
+	if strings.Count(got, "<code>") != 2 {
+		t.Fatalf("expected 2 inline code tags, got: %q", got)
+	}
+	if !strings.Contains(got, "<code>foo</code>") || !strings.Contains(got, "<code>bar</code>") {
+		t.Fatalf("missing inline code contents, got: %q", got)
+	}
+}