diff --git a/ansi/wrap.go b/ansi/wrap.go
index 530be6ca..d2b2ace2 100644
--- a/ansi/wrap.go
+++ b/ansi/wrap.go
@@ -196,6 +196,12 @@ func wordwrap(m Method, s string, limit int, breakpoints string) string {
 				addWord()
 				space.WriteRune(r)
 			} else if bytes.ContainsAny(cluster, breakpoints) {
+				// Treat the current word + breakpoint as one unit:
+				// if appending it would overflow the line, break first
+				// so the word doesn't trail past the limit.
+				if curWidth+space.Len()+wordLen+1 > limit && wordLen+1 <= limit {
+					addNewline()
+				}
 				addSpace()
 				addWord()
 				buf.Write(cluster)
@@ -235,6 +241,9 @@ func wordwrap(m Method, s string, limit int, breakpoints string) string {
 			case r == '-':
 				fallthrough
 			case runeContainsAny(r, breakpoints):
+				if curWidth+space.Len()+wordLen+1 > limit && wordLen+1 <= limit {
+					addNewline()
+				}
 				addSpace()
 				addWord()
 				buf.WriteByte(b[i])
diff --git a/ansi/wrap_test.go b/ansi/wrap_test.go
index 65c12ebc..711b471d 100644
--- a/ansi/wrap_test.go
+++ b/ansi/wrap_test.go
@@ -63,6 +63,7 @@ var wwCases = []struct {
 	{"emoji_breakpoint", "foo😃 foobar", 4, "😃", "foo😃\nfoobar"},
 	{"wide_emoji_breakpoint", "foo🫧 foobar", 4, "🫧", "foo🫧\nfoobar"},
 	{"space_breakpoint", "foo --bar", 9, "-", "foo --bar"},
+	{"breakpoint_overflow", "foo bar, fo", 7, ",", "foo\nbar, fo"},
 	{"simple", "foo bars foobars", 4, "", "foo\nbars\nfoobars"},
 	{"limit", "foo bar", 5, "", "foo\nbar"},
 	{"remove white spaces", "foo    \nb   ar   ", 4, "", "foo\nb\nar"},