diff --git a/twitter2bsky_daemon.py b/twitter2bsky_daemon.py
index 2b014fa..e4571be 100644
--- a/twitter2bsky_daemon.py
+++ b/twitter2bsky_daemon.py
@@ -368,6 +368,64 @@ def looks_like_title_plus_url_post(text):
     return len(urls_in_last_line) == 1 and len(total_urls) == 1 and last_line.startswith(("http://", "https://"))
 
 
+def find_tail_preservation_start(text, primary_non_x_url):
+    if not text or not primary_non_x_url:
+        return None
+
+    url_pos = text.find(primary_non_x_url)
+    if url_pos == -1:
+        return None
+
+    hashtag_match = re.search(r"\s#[^\s#]+", text[url_pos:])
+    has_hashtag_after_url = hashtag_match is not None
+
+    candidates = [url_pos]
+
+    # Prefer clause boundaries before the URL.
+    clause_patterns = [
+        r"\.\s+",
+        r":\s+",
+        r";\s+",
+        r"!\s+",
+        r"\?\s+",
+        r",\s+",
+    ]
+
+    before = text[:url_pos]
+    for pattern in clause_patterns:
+        for match in re.finditer(pattern, before):
+            candidates.append(match.end())
+
+    # Prefer previous line break if present.
+    last_newline = before.rfind("\n")
+    if last_newline != -1:
+        candidates.append(last_newline + 1)
+
+    # If there are hashtags after the URL, preserve a more generous block before it.
+    if has_hashtag_after_url:
+        generous_start = max(0, url_pos - 120)
+        while generous_start > 0 and text[generous_start] not in {" ", "\n"}:
+            generous_start -= 1
+        candidates.append(generous_start)
+
+    # Choose the closest reasonable boundary before the URL, but not too close.
+    reasonable_candidates = [
+        c for c in candidates
+        if 0 <= c < url_pos and (url_pos - c) <= 180
+    ]
+
+    if reasonable_candidates:
+        start = min(reasonable_candidates, key=lambda c: (url_pos - c))
+        # If the nearest boundary is too close, fall back to a slightly earlier one.
+        if url_pos - start < 35:
+            farther = [c for c in reasonable_candidates if url_pos - c >= 35]
+            if farther:
+                start = min(farther, key=lambda c: (url_pos - c))
+        return start
+
+    return url_pos
+
+
 def looks_like_url_and_tag_tail(text, primary_non_x_url=None):
     if not text or not primary_non_x_url:
         return False
@@ -381,17 +439,9 @@ def looks_like_url_and_tag_tail(text, primary_non_x_url=None):
     if not tail.startswith(("http://", "https://")):
         return False
 
-    # URL followed by optional hashtags / trailing words is a meaningful tail we should try to preserve.
     if re.search(r"https?://\S+.*#[^\s#]+", tail):
         return True
 
-    # Also treat URL preceded by meaningful text ending as important if the URL is not on its own line.
-    lines = [line.strip() for line in repaired.splitlines() if line.strip()]
-    if lines:
-        for line in lines:
-            if primary_non_x_url in line and not line.startswith(("http://", "https://")):
-                return True
-
     return False
 
 
@@ -417,10 +467,16 @@ def truncate_text_preserving_tail(text, tail_start, max_length=BSKY_TEXT_MAX_LEN
     if not tail:
         return truncate_text_safely(text, max_length)
 
-    # Need room for "... " + tail
     reserve = len(tail) + 4
     if reserve >= max_length:
-        return truncate_text_safely(text, max_length)
+        # Tail too large; keep the tail itself and trim from its front carefully.
+        shortened_tail = tail
+        if len(shortened_tail) > max_length - 3:
+            shortened_tail = shortened_tail[-(max_length - 3):]
+            first_space = shortened_tail.find(" ")
+            if first_space > 0 and first_space < 40:
+                shortened_tail = shortened_tail[first_space + 1:]
+        return "..." + shortened_tail[-(max_length - 3):]
 
     available_prefix = max_length - reserve
     prefix = text[:tail_start].rstrip()
@@ -447,17 +503,15 @@ def choose_final_visible_text(full_clean_text, primary_non_x_url=None, prefer_fu
         return text
 
     if primary_non_x_url:
-        # If the URL and hashtag tail are semantically important, preserve the tail first.
-        if looks_like_url_and_tag_tail(text, primary_non_x_url):
-            url_pos = text.find(primary_non_x_url)
-            if url_pos != -1:
-                preserved = truncate_text_preserving_tail(text, url_pos, BSKY_TEXT_MAX_LENGTH)
-                if preserved and len(preserved) <= BSKY_TEXT_MAX_LENGTH:
-                    logging.info("🔗 Preserving meaningful URL/tag tail in visible Bluesky text")
-                    return preserved
+        tail_start = find_tail_preservation_start(text, primary_non_x_url)
 
-        # For article-card-style posts, prefer removing the URL entirely from visible text.
-        if prefer_full_text_without_url:
+        if tail_start is not None:
+            preserved = truncate_text_preserving_tail(text, tail_start, BSKY_TEXT_MAX_LENGTH)
+            if preserved and len(preserved) <= BSKY_TEXT_MAX_LENGTH:
+                logging.info("🔗 Preserving meaningful ending block with URL/hashtags in visible Bluesky text")
+                return preserved
+
+        if prefer_full_text_without_url and not looks_like_url_and_tag_tail(text, primary_non_x_url):
             text_without_url = remove_url_from_visible_text(text, primary_non_x_url).strip()
             if text_without_url and len(text_without_url) <= BSKY_TEXT_MAX_LENGTH:
                 logging.info("🔗 Keeping full visible text by removing long external URL from body and using external card")