diff --git a/service/domain/content/lexer.go b/service/domain/content/lexer.go
index f560280..9c2a623 100644
--- a/service/domain/content/lexer.go
+++ b/service/domain/content/lexer.go
@@ -8,6 +8,15 @@ import (
 	"github.com/boreq/errors"
 )
 
+const (
+	httpColonSlashSlash  = "http://"
+	httpsColonSlashSlash = "https://"
+	nostrColon           = "nostr:"
+	nevent               = "nevent"
+	npub                 = "npub"
+	note                 = "note"
+)
+
 type Token struct {
 	Type TokenType
 	Text string
@@ -168,15 +177,6 @@ func (l *Lexer) mergeConsecutiveTexts(tokens []Token) []Token {
 
 type stateFn func(l *Lexer) (stateFn, error)
 
-const (
-	httpColonSlashSlash  = "http://"
-	httpsColonSlashSlash = "https://"
-	nostrColon           = "nostr:"
-	nevent               = "nevent"
-	npub                 = "npub"
-	note                 = "note"
-)
-
 func stateText(l *Lexer) (stateFn, error) {
 	for {
 		if l.comesNext(httpColonSlashSlash) || l.comesNext(httpsColonSlashSlash) {
@@ -295,7 +295,7 @@ func stateNostrLinkData(l *Lexer) (stateFn, error) {
 }
 
 func isValidLinkCharacterExcludingDot(r rune) bool {
-	return unicode.IsLetter(r) || unicode.IsNumber(r) || r == '%'
+	return unicode.IsLetter(r) || unicode.IsNumber(r) || r == '%' || r == '/'
 }
 
 func isBech32(r rune) bool {
diff --git a/service/domain/content/lexer_test.go b/service/domain/content/lexer_test.go
index 0196bc1..a643036 100644
--- a/service/domain/content/lexer_test.go
+++ b/service/domain/content/lexer_test.go
@@ -133,6 +133,16 @@ func TestLexer(t *testing.T) {
 				},
 			},
 		},
+		{
+			Name: "only_link_with_path",
+			In:   `https://example.com/path`,
+			Out: []content.Token{
+				{
+					Type: content.TokenTypeLink,
+					Text: "https://example.com/path",
+				},
+			},
+		},
 	}
 
 	for _, testCase := range testCases {
diff --git a/service/domain/tweet_generator.go b/service/domain/tweet_generator.go
index a5560c2..a146b6b 100644
--- a/service/domain/tweet_generator.go
+++ b/service/domain/tweet_generator.go
@@ -3,6 +3,7 @@ package domain
 import (
 	"fmt"
 	"strings"
+	"unicode/utf8"
 
 	"github.com/boreq/errors"
 	"github.com/planetary-social/nos-crossposting-service/service/domain/content"
@@ -70,17 +71,16 @@ func (g *TweetGenerator) createContent(builder *strings.Builder, elements []cont
 
 			builder.WriteString(element.Text)
 		case content.ElementTypeText:
-			for i, part := range strings.Split(element.Text, " ") {
-				futureTotalLength := builder.Len() + len(part)
-				if futureTotalLength > noteContentMaxLengthInRunes {
-					builder.WriteString(ellipsis)
+			remainingLen := noteContentMaxLengthInRunes - utf8.RuneCountInString(builder.String())
+			numberOfWrittenRunes := 0
+			for _, r := range element.Text {
+				builder.WriteRune(r)
+				numberOfWrittenRunes++
+
+				if numberOfWrittenRunes >= remainingLen {
+					builder.WriteString("...")
 					return nil
 				}
-
-				if i > 0 {
-					builder.WriteString(" ")
-				}
-				builder.WriteString(part)
 			}
 		default:
 			return errors.New("unknown element")
diff --git a/service/domain/tweet_generator_test.go b/service/domain/tweet_generator_test.go
index e49f904..c4cd865 100644
--- a/service/domain/tweet_generator_test.go
+++ b/service/domain/tweet_generator_test.go
@@ -29,6 +29,17 @@ func TestTweetGenerator(t *testing.T) {
 			},
 			ExpectedContent: "Some text.",
 		},
+		{
+			Name: "not_a_reply_long_without_spaces",
+			Event: nostr.Event{
+				Kind: domain.EventKindNote.Int(),
+				Tags: []nostr.Tag{
+					[]string{"p", fixtures.SomePublicKey().Hex()},
+				},
+				Content: strings.Repeat("a", 300),
+			},
+			ExpectedContent: strings.Repeat("a", 200) + "...",
+		},
 		{
 			Name: "not_a_reply_long",
 			Event: nostr.Event{
@@ -38,7 +49,18 @@ func TestTweetGenerator(t *testing.T) {
 				},
 				Content: strings.Repeat("Some text. ", 100),
 			},
-			ExpectedContent: "Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text....",
+			ExpectedContent: "Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. Some text. So...",
+		},
+		{
+			Name: "not_a_reply_huge_link",
+			Event: nostr.Event{
+				Kind: domain.EventKindNote.Int(),
+				Tags: []nostr.Tag{
+					[]string{"p", fixtures.SomePublicKey().Hex()},
+				},
+				Content: "https://example.com/" + strings.Repeat("a", 300),
+			},
+			ExpectedContent: "...",
 		},
 		{
 			Name: "reply",