diff --git a/main.go b/main.go
index e3c97e2..83cc5f0 100644
--- a/main.go
+++ b/main.go
@@ -30,6 +30,11 @@ const maxImagesPerPost = 4
 // Bluesky rejects blobs over 2,000,000 bytes; Twitter allows up to 5MB.
 const maxImageBytes = 2_000_000
 
+// urlLength is what a link costs against maxTweetLength: Twitter rewrites
+// every URL to a t.co address of this fixed length, however long the original
+// was, so counting the raw characters would reject messages it would accept.
+const urlLength = 23
+
 // urlPattern picks candidate links out of message text; each one is parsed
 // properly before it is judged to be a YouTube link.
 var urlPattern = regexp.MustCompile(`https?://[^\s<>"']+`)
@@ -39,6 +44,17 @@ func trimURL(match string) string {
 	return strings.TrimRight(match, ".,!?、。)]}>")
 }
 
+// tweetLength counts a message the way Twitter does, charging every link a
+// fixed length instead of its actual one.
+func tweetLength(content string) int {
+	length := utf8.RuneCountInString(content)
+	for _, match := range urlPattern.FindAllString(content, -1) {
+		// The trimmed punctuation is still ordinary text and keeps counting.
+		length += urlLength - utf8.RuneCountInString(trimURL(match))
+	}
+	return length
+}
+
 var httpClient = &http.Client{Timeout: 30 * time.Second}
 
 // shrinkImage re-encodes (and if necessary downscales) an image until it
@@ -145,8 +161,8 @@ func (dist *distributor) reportf(format string, args ...any) {
 // created posts a new Discord message to every output, as a reply when the
 // Discord message itself was a reply to something we already distributed.
 func (dist *distributor) created(event discord.Event) {
-	if length := utf8.RuneCountInString(event.Content); length > maxTweetLength {
-		dist.reportf("Error: message is %d characters, exceeding the %d character limit; not posted", length, maxTweetLength)
+	if length := tweetLength(event.Content); length > maxTweetLength {
+		dist.reportf("Error: message is %d characters counting each link as %d, exceeding the %d character limit; not posted", length, urlLength, maxTweetLength)
 		return
 	}
 
diff --git a/main_test.go b/main_test.go
index 7908a98..4ae3e42 100644
--- a/main_test.go
+++ b/main_test.go
@@ -6,8 +6,10 @@ import (
 	"image/color"
 	"image/jpeg"
 	"math/rand"
+	"strings"
 	"testing"
 	"tweetdistributor/output"
+	"unicode/utf8"
 )
 
 // noiseJPEG returns a JPEG image of random noise, which compresses poorly
@@ -28,6 +30,42 @@ func noiseJPEG(t *testing.T, width, height int) []byte {
 	return buf.Bytes()
 }
 
+func TestTweetLength(t *testing.T) {
+	tests := []struct {
+		name    string
+		content string
+		want    int
+	}{
+		{"no link", "こんにちは", 5},
+		{"long link", "https://www.youtube.com/watch?v=dQw4w9WgXcQ&list=PLabcdefghijklmnop", urlLength},
+		{"short link", "https://a.jp", urlLength},
+		{"link with text", "みてね " + strings.Repeat("x", 10) + " https://youtu.be/dQw4w9WgXcQ", 4 + 10 + 1 + urlLength},
+		{"two links", "https://a.jp https://b.jp", urlLength*2 + 1},
+		{"trailing punctuation still counts", "https://a.jp。", urlLength + 1},
+		{"multibyte path", "https://ja.wikipedia.org/wiki/日本語", urlLength},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			if got := tweetLength(tt.content); got != tt.want {
+				t.Errorf("tweetLength(%q) = %d, want %d", tt.content, got, tt.want)
+			}
+		})
+	}
+}
+
+func TestTweetLengthAcceptsMessageOnlyLinksMakeTooLong(t *testing.T) {
+	// A message that the raw rune count would reject but Twitter accepts.
+	content := strings.Repeat("あ", 100) + " https://www.youtube.com/watch?v=dQw4w9WgXcQ&t=120s"
+
+	if raw := utf8.RuneCountInString(content); raw <= maxTweetLength {
+		t.Fatalf("test message should be %d raw characters, got %d", maxTweetLength+1, raw)
+	}
+	if got := tweetLength(content); got > maxTweetLength {
+		t.Errorf("tweetLength = %d, want it to fit within %d", got, maxTweetLength)
+	}
+}
+
 func TestShrinkImageLarge(t *testing.T) {
 	data := noiseJPEG(t, 3000, 3000)
 	if len(data) <= maxImageBytes {