diff --git a/ext/fts5/fts5_index.c b/ext/fts5/fts5_index.c
index ed919298e7..8804e94bb0 100644
--- a/ext/fts5/fts5_index.c
+++ b/ext/fts5/fts5_index.c
@@ -3038,13 +3038,19 @@ static int fts5IndexTombstoneQuery(
   return 0;
 }
 
+/*
+** Return true if the iterator passed as the only argument points
+** to an segment entry for which there is a tombstone. Return false
+** if there is no tombstone or if the iterator is already at EOF.
+*/
 static int fts5MultiIterIsDeleted(Fts5Iter *pIter){
   int iFirst = pIter->aFirst[1].iFirst;
   Fts5SegIter *pSeg = &pIter->aSeg[iFirst];
 
-  if( pSeg->nTombstone ){
+  if( pSeg->pLeaf && pSeg->nTombstone ){
     /* Figure out which page the rowid might be present on. */
-    int iPg = pSeg->iRowid % pSeg->nTombstone;
+    int iPg = ((u64)pSeg->iRowid) % pSeg->nTombstone;
+    assert( iPg>=0 );
 
     if( pSeg->apTombstone[iPg]==0 ){
       pSeg->apTombstone[iPg] = fts5DataRead(pIter->pIndex,
@@ -6428,7 +6434,12 @@ int sqlite3Fts5IndexGetOrigin(Fts5Index *p, i64 *piOrigin){
 /*
 ** Buffer pPg contains a page of a tombstone hash table - one of nPg.
 */
-static int fts5IndexTombstoneAddToPage(Fts5Data *pPg, int nPg, u64 iRowid){
+static int fts5IndexTombstoneAddToPage(
+  Fts5Data *pPg, 
+  int bForce,
+  int nPg, 
+  u64 iRowid
+){
   int szKey = TOMBSTONE_KEYSIZE(pPg);
   int nSlot = (pPg->nn - 8) / szKey;
   int iSlot = (iRowid / nPg) % nSlot;
@@ -6440,6 +6451,10 @@ static int fts5IndexTombstoneAddToPage(Fts5Data *pPg, int nPg, u64 iRowid){
     return 0;
   }
 
+  if( bForce==0 && nElem>=(nSlot/2) ){
+    return 1;
+  }
+
   fts5PutU32(&pPg->p[4], nElem+1);
   if( szKey==4 ){
     u32 *aSlot = (u32*)&pPg->p[8];
@@ -6451,7 +6466,7 @@ static int fts5IndexTombstoneAddToPage(Fts5Data *pPg, int nPg, u64 iRowid){
     fts5PutU64((u8*)&aSlot[iSlot], iRowid);
   }
 
-  return nElem >= (nSlot/2);
+  return 0;
 }
 
 /*
@@ -6489,7 +6504,7 @@ static int fts5IndexTombstoneRehash(
     }
 
     if( pData ){
-      int szKeyIn = pData->p[3] ? 8 : 4;
+      int szKeyIn = TOMBSTONE_KEYSIZE(pData);
       int nSlotIn = (pData->nn - 8) / szKeyIn;
       int iIn;
       for(iIn=0; iIn<nSlotIn; iIn++){
@@ -6507,7 +6522,7 @@ static int fts5IndexTombstoneRehash(
         /* If iVal is not 0 at this point, insert it into the new hash table */
         if( iVal ){
           Fts5Data *pPg = apOut[(iVal % nOut)];
-          res = fts5IndexTombstoneAddToPage(pPg, nOut, iVal);
+          res = fts5IndexTombstoneAddToPage(pPg, 0, nOut, iVal);
           if( res ) break;
         }
       }
@@ -6642,7 +6657,6 @@ static void fts5IndexTombstoneAdd(
   Fts5Data *pPg = 0;
   int iPg = -1;
   int szKey = 0;
-
   int nHash = 0;
   Fts5Data **apHash = 0;
 
@@ -6654,7 +6668,7 @@ static void fts5IndexTombstoneAdd(
       return;
     }
 
-    if( 0==fts5IndexTombstoneAddToPage(pPg, pSeg->nPgTombstone, iRowid) ){
+    if( 0==fts5IndexTombstoneAddToPage(pPg, 0, pSeg->nPgTombstone, iRowid) ){
       fts5DataWrite(p, FTS5_TOMBSTONE_ROWID(pSeg->iSegid,iPg), pPg->p, pPg->nn);
       fts5DataRelease(pPg);
       return;
@@ -6673,7 +6687,7 @@ static void fts5IndexTombstoneAdd(
   ** table pages, then write them all out to disk. */
   if( nHash ){
     int ii = 0;
-    fts5IndexTombstoneAddToPage(apHash[iRowid % nHash], nHash, iRowid);
+    fts5IndexTombstoneAddToPage(apHash[iRowid % nHash], 1, nHash, iRowid);
     for(ii=0; ii<nHash; ii++){
       i64 iTombstoneRowid = FTS5_TOMBSTONE_ROWID(pSeg->iSegid, ii);
       fts5DataWrite(p, iTombstoneRowid, apHash[ii]->p, apHash[ii]->nn);
@@ -7544,7 +7558,26 @@ static void fts5DecodeFunction(
     }
   }else if( bTomb ){
     u32 nElem  = fts5GetU32(&a[4]);
+    int szKey = (aBlob[0]==4 || aBlob[0]==8) ? aBlob[0] : 8;
+    int nSlot = (n - 8) / szKey;
+    int ii;
     sqlite3Fts5BufferAppendPrintf(&rc, &s, " nElem=%d", (int)nElem);
+    if( aBlob[1] ){
+      sqlite3Fts5BufferAppendPrintf(&rc, &s, " 0");
+    }
+    for(ii=0; ii<nSlot; ii++){
+      u64 iVal = 0;
+      if( szKey==4 ){
+        u32 *aSlot = (u32*)&aBlob[8];
+        if( aSlot[ii] ) iVal = fts5GetU32((u8*)&aSlot[ii]);
+      }else{
+        u64 *aSlot = (u64*)&aBlob[8];
+        if( aSlot[ii] ) iVal = fts5GetU64((u8*)&aSlot[ii]);
+      }
+      if( iVal!=0 ){
+        sqlite3Fts5BufferAppendPrintf(&rc, &s, " %lld", (i64)iVal);
+      }
+    }
   }else if( iSegid==0 ){
     if( iRowid==FTS5_AVERAGES_ROWID ){
       fts5DecodeAverages(&rc, &s, a, n);
diff --git a/ext/fts5/test/fts5contentless2.test b/ext/fts5/test/fts5contentless2.test
new file mode 100644
index 0000000000..c9e93c6600
--- /dev/null
+++ b/ext/fts5/test/fts5contentless2.test
@@ -0,0 +1,152 @@
+# 2023 July 19
+#
+# The author disclaims copyright to this source code.  In place of
+# a legal notice, here is a blessing:
+#
+#    May you do good and not evil.
+#    May you find forgiveness for yourself and forgive others.
+#    May you share freely, never taking more than you give.
+#
+#***********************************************************************
+#
+# This file contains tests for the content= and content_rowid= options.
+#
+
+source [file join [file dirname [info script]] fts5_common.tcl]
+set testprefix fts5contentless2
+
+# If SQLITE_ENABLE_FTS5 is defined, omit this file.
+ifcapable !fts5 {
+  finish_test
+  return
+}
+
+proc vocab {} {
+  list aaa bbb ccc ddd eee fff ggg hhh iii jjj kkk lll mmm nnn ooo ppp
+}
+
+proc document {nToken} {
+  set doc [list]
+  set vocab [vocab]
+  for {set ii 0} {$ii < $nToken} {incr ii} {
+    lappend doc [lindex $vocab [expr int(rand()*[llength $vocab])]]
+  }
+  set doc
+}
+db func document document
+
+proc contains {doc token} {
+  expr {[lsearch $doc $token]>=0}
+}
+db func contains contains
+
+proc do_compare_tables_test {tn} {
+  uplevel [list do_test $tn {
+    foreach v [vocab] {
+      set l1 [execsql { SELECT rowid FROM t1 WHERE contains(doc, $v) }]
+      set l2 [execsql { SELECT rowid FROM t2($v) }]
+      if {$l1!=$l2} { error "1: query mismatch ($l1) ($l2)" }
+
+      set w "[string range $v 0 1]*"
+      set l1 [execsql { SELECT rowid FROM t1 WHERE contains(doc, $w) }]
+      set l2 [execsql { SELECT rowid FROM t2($w) }]
+      if {$l1!=$l2} { error "2: query mismatch ($l1) ($l2)" }
+
+      set w "[string range $v 0 0]*"
+      set l1 [execsql { SELECT rowid FROM t1 WHERE contains(doc, $w) }]
+      set l2 [execsql { SELECT rowid FROM t2($w) }]
+      if {$l1!=$l2} { error "2: query mismatch ($l1) ($l2)" }
+
+      set l1 [execsql { 
+        SELECT rowid FROM t1 WHERE contains(doc, $v) ORDER BY rowid DESC 
+      }]
+      set l2 [execsql { SELECT rowid FROM t2($v) ORDER BY rowid DESC }]
+      if {$l1!=$l2} { error "1: query mismatch ($l1) ($l2)" }
+    }
+    set {} {}
+  } {}]
+}
+
+proc lshuffle {in} {
+  set L [list]
+  set ret [list]
+  foreach elem $in { lappend L [list [expr rand()] $elem] }
+  foreach pair [lsort -index 0 $L] { lappend ret [lindex $pair 1] }
+  set ret
+}
+
+expr srand(0)
+
+do_execsql_test 1.0 {
+  CREATE VIRTUAL TABLE t2 USING fts5(
+      doc, prefix=2, content=, contentless_delete=1
+  );
+
+  CREATE TABLE t1(doc);
+  CREATE TRIGGER tr1 AFTER DELETE ON t1 BEGIN
+    DELETE FROM t2 WHERE rowid = old.rowid;
+  END;
+}
+
+set SMALLEST64 -9223372036854775808
+set LARGEST64   9223372036854775807
+
+foreach {tn r1 r2} {
+  1   0               50
+  2   $SMALLEST64     $SMALLEST64+50
+  3   $LARGEST64-50   $LARGEST64
+  4   -50             -1
+} {
+  set r1 [expr $r1]
+  set r2 [expr $r2]
+
+  do_test 1.1.$tn {
+    execsql BEGIN
+    for {set ii $r1} {$ii <= $r2} {incr ii} {
+      execsql { INSERT INTO t1(rowid, doc) VALUES ($ii, document(8)); }
+    }
+    execsql COMMIT
+  } {}
+}
+do_test 1.2 {
+  db eval { SELECT rowid, doc FROM t1 } {
+    execsql { INSERT INTO t2(rowid, doc) VALUES($rowid, $doc) }
+  }
+} {}
+
+foreach {tn rowid} {
+  1  $SMALLEST64
+  2  0
+  3  -5
+  4  -30
+  5  $LARGEST64
+  6  $LARGEST64-1
+} {
+  set rowid [expr $rowid]
+  do_execsql_test 1.3.$tn.1 {
+    DELETE FROM t1 WHERE rowid=$rowid
+  }
+  do_compare_tables_test 1.3.$tn.2
+}
+
+set iTest 1
+foreach r [lshuffle [execsql {SELECT rowid FROM t1}]] {
+  if {($iTest % 50)==0} {
+    execsql { INSERT INTO t2(t2) VALUES('optimize') }
+  }
+  if {($iTest % 5)==0} {
+    execsql { INSERT INTO t2(t2, rank) VALUES('merge', 5) }
+  }
+  do_execsql_test 1.4.$iTest.1($r) {
+    DELETE FROM t1 WHERE rowid=$r
+  }
+  do_compare_tables_test 1.4.$iTest.2
+  incr iTest
+}
+
+do_execsql_test 1.5 {
+  SELECT * FROM t1
+} {}
+
+finish_test
+
diff --git a/manifest b/manifest
index b2e058d24d..53072385c5 100644
--- a/manifest
+++ b/manifest
@@ -1,5 +1,5 @@
-C Merge\sthe\sFTS5\smemory\sleak\sfix\sfrom\strunk.
-D 2023-07-18T17:43:47.072
+C Fix\svarious\sproblems\swith\sfts5\scontentless_delete=1\stables.
+D 2023-07-18T19:52:32.733
 F .fossil-settings/empty-dirs dbb81e8fc0401ac46a1491ab34a7f2c7c0452f2f06b54ebb845d024ca8283ef1
 F .fossil-settings/ignore-glob 35175cdfcf539b2318cb04a9901442804be81cd677d8b889fcc9149c21f239ea
 F LICENSE.md df5091916dbb40e6e9686186587125e1b2ff51f022cc334e886c19a0e9982724
@@ -92,7 +92,7 @@ F ext/fts5/fts5_buffer.c 3001fbabb585d6de52947b44b455235072b741038391f830d6b7292
 F ext/fts5/fts5_config.c 010fabcc0aaa0dfa76b19146e8bddf7de368933eeac01e294af6607447500caa
 F ext/fts5/fts5_expr.c 2473c13542f463cae4b938c498d6193c90d38ea1a2a4f9849c0479736e50d24d
 F ext/fts5/fts5_hash.c d4fb70940359f2120ccd1de7ffe64cc3efe65de9e8995b822cd536ff64c96982
-F ext/fts5/fts5_index.c 78c234c47a4870dd8dad7289f457188b8b8c039ce6ecf0e1d8aea0d369857522
+F ext/fts5/fts5_index.c a2e081dcffed12da4ec2a03429da368d8d0a980ddbed1324cd00f028fb510c48
 F ext/fts5/fts5_main.c ede405f0f11db562653b988d043a531daa66093b46c1b35b8fcddb54819cba84
 F ext/fts5/fts5_storage.c 7d22c8ea1d484134bd715f55b370ae9b5a830b627986344c4ffa532c3e89186b
 F ext/fts5/fts5_tcl.c b1445cbe69908c411df8084a10b2485500ac70a9c747cdc8cda175a3da59d8ae
@@ -133,6 +133,7 @@ F ext/fts5/test/fts5conflict.test 655925678e630d3cdf145d18725a558971806416f453ac
 F ext/fts5/test/fts5connect.test 08030168fc96fc278fa81f28654fb7e90566f33aff269c073e19b3ae9126b2f4
 F ext/fts5/test/fts5content.test 213506436fb2c87567b8e31f6d43ab30aab99354cec74ed679f22aad0cdbf283
 F ext/fts5/test/fts5contentless.test 9a42a86822670792ba632f5c57459addeb774d93b29d5e6ddae08faa64c2b6d9
+F ext/fts5/test/fts5contentless2.test 61ce8780ac933fb52bbba4191c33cc1f97bfa96eb7c1a7a2d6338c4bcfa6916a
 F ext/fts5/test/fts5corrupt.test 77ae6f41a7eba10620efb921cf7dbe218b0ef232b04519deb43581cb17a57ebe
 F ext/fts5/test/fts5corrupt2.test 7453752ba12ce91690c469a6449d412561cc604b1dec994e16ab132952e7805f
 F ext/fts5/test/fts5corrupt3.test 7da9895dafa404efd20728f66ff4b94399788bdc042c36fe2689801bba2ccd78
@@ -2044,8 +2045,8 @@ F vsixtest/vsixtest.tcl 6a9a6ab600c25a91a7acc6293828957a386a8a93
 F vsixtest/vsixtest.vcxproj.data 2ed517e100c66dc455b492e1a33350c1b20fbcdc
 F vsixtest/vsixtest.vcxproj.filters 37e51ffedcdb064aad6ff33b6148725226cd608e
 F vsixtest/vsixtest_TemporaryKey.pfx e5b1b036facdb453873e7084e1cae9102ccc67a0
-P 5f66eb4e2603278dcc9dbfe4bf506cba1aa03180cfb492a0dfc3a8be32cc994b 4dcad2db743fdb9ef72871ca5a4d1384f76cb697161b0f5110e2670a83a18e8a
-R 6df4842f998a408f262f6f4830fd595f
-U drh
-Z 63584765e02f480fe2927dfa6f8c1662
+P fb65cb73d7ea22a8b20dccfa3abdaaa809eee4fcee6fe4846bd2e598ceb49aa4
+R 0b35403fc3d2abc67db6df3c073d3f31
+U dan
+Z c153ae75657e3c69ee3dd162b0a421d3
 # Remove this line to create a well-formed Fossil manifest.
diff --git a/manifest.uuid b/manifest.uuid
index 28852ffb55..aa3336730e 100644
--- a/manifest.uuid
+++ b/manifest.uuid
@@ -1 +1 @@
-fb65cb73d7ea22a8b20dccfa3abdaaa809eee4fcee6fe4846bd2e598ceb49aa4
\ No newline at end of file
+0d005112b8aca9e9eca9d86d5fed9168f6a0218fd290b5489b9e7b05714610f4
\ No newline at end of file