diff --git a/manifest b/manifest
index cdb56994ed..071177a7fa 100644
--- a/manifest
+++ b/manifest
@@ -1,5 +1,5 @@
-C Do\snot\sattempt\sto\srun\snew\stest\sfile\srbupass.test\sif\sthe\s"demo"\sVFS\sis\snot\savailable.
-D 2023-01-12T19:28:34.870
+C Enhance\squery\splanning\sso\sthat\sit\scheck\sfor\ssqlite3_interrupt()\scalls\sand\nperiodically\sinvokes\sthe\sprogress\shandler\scallback\s(if\sany)\sduring\slong\nquery\sanalyses.
+D 2023-01-13T15:54:25.723
 F .fossil-settings/empty-dirs dbb81e8fc0401ac46a1491ab34a7f2c7c0452f2f06b54ebb845d024ca8283ef1
 F .fossil-settings/ignore-glob 35175cdfcf539b2318cb04a9901442804be81cd677d8b889fcc9149c21f239ea
 F LICENSE.md df5091916dbb40e6e9686186587125e1b2ff51f022cc334e886c19a0e9982724
@@ -646,16 +646,16 @@ F src/printf.c ff4b05e38bf928ff1b80d3dda4f977b10fe39ecbfe69c018224c7e5594fb2455
 F src/random.c 606b00941a1d7dd09c381d3279a058d771f406c5213c9932bbd93d5587be4b9c
 F src/resolve.c efea4e5fbecfd6d0a9071b0be0d952620991673391b6ffaaf4c277b0bb674633
 F src/rowset.c ba9515a922af32abe1f7d39406b9d35730ed65efab9443dc5702693b60854c92
-F src/select.c 146222acbf9ea4e7f99c45a9e3cb4a0ba7e02c4f0df5186094ea1f9ea9907a02
+F src/select.c d389ccdb96855dbfaadc22d936889e1f0652ffca17e31a6b6522b45d99daa8ce
 F src/shell.c.in f7c75d1a9f900516e40f17f040668d5797592344bd88cff7ee7df586de6893c6
-F src/sqlite.h.in 231d505c86ac4688b82259529273fe5fb2cce86cb80ea50628ff776113b5c706
+F src/sqlite.h.in 9a24b7e0f91412a1afe56f2be3c94857438f9e5e9bd91b4ec8ecc0ced9e9e6ed
 F src/sqlite3.rc 5121c9e10c3964d5755191c80dd1180c122fc3a8
 F src/sqlite3ext.h da473ce2b3d0ae407a6300c4a164589b9a6bfdbec9462688a8593ff16f3bb6e4
-F src/sqliteInt.h 079ccd9c161f4b74967188fd6321810159fdc4c32371b68559719828fac20f43
+F src/sqliteInt.h 43eeee1ea80543a0e40444bf53643ca259a2b1158ccfe859a6a6435b7358ecdd
 F src/sqliteLimit.h d7323ffea5208c6af2734574bae933ca8ed2ab728083caa117c9738581a31657
 F src/status.c 160c445d7d28c984a0eae38c144f6419311ed3eace59b44ac6dafc20db4af749
 F src/table.c 0f141b58a16de7e2fbe81c308379e7279f4c6b50eb08efeec5892794a0ba30d1
-F src/tclsqlite.c 4e64ba300a5a26e0f1170e09032429faeb65e45e8f3d1a7833e8edb69fc2979e
+F src/tclsqlite.c 8522a04fb9c84faa1d80354430ae0ee9349727a3a4b32e3cfe39b9be8324cabd
 F src/test1.c 39c13c25f5c4e75a07cb6bd34cfc1b8aa97ecc6f80f08953fa164db7e92ce71e
 F src/test2.c 827446e259a3b7ab949da1542953edda7b5117982576d3e6f1c24a0dd20a5cef
 F src/test3.c 61798bb0d38b915067a8c8e03f5a534b431181f802659a6616f9b4ff7d872644
@@ -716,13 +716,13 @@ F src/trigger.c 5e68b790f022b8dafbfb0eb244786512a95c9575fc198719d2557d73e5795858
 F src/update.c f118e51768d2c1309e3c81e9f91141b22b8a1339cbc5969b1b2d810feaa25b22
 F src/upsert.c 5303dc6c518fa7d4b280ec65170f465c7a70b7ac2b22491598f6d0b4875b3145
 F src/utf.c ee39565f0843775cc2c81135751ddd93eceb91a673ea2c57f61c76f288b041a0
-F src/util.c 0e5cf9062a796f0f1b6b3228b121b2344932c05425f7c8b5a7cb245812473bbd
+F src/util.c 3ff7bc2b48dd425b1448304bb86273b05da1621f136d51dbb9789f8803559a1f
 F src/vacuum.c 84ce7f01f8a7a08748e107a441db83bcec13970190ddcb0c9ff522adbc1c23fd
 F src/vdbe.c 238635c1c40d42d9ded72994b81d4127f99d6d09e9279bdd37f6f34f4025adee
 F src/vdbe.h 73b904a6b3bb27f308c6cc287a5751ebc7f1f89456be0ed068a12b92844c6e8c
 F src/vdbeInt.h fc15815b7bdafbb27e7f027faba2b0112e87d382c0d72241672528806ebc0db5
 F src/vdbeapi.c 4ee67890913c1d2469c68e3ad2e7ddeab57ac5924a64bbfd0906a8ea0d542c7f
-F src/vdbeaux.c 9eb7394126b88e55f81321d5e87636e0cd5e5856818d644d8abd6bfbb9c0be9d
+F src/vdbeaux.c 3f9e3b6585e7434aa11300169dd66ddf0fc963a0c6f7940bdc058335dadeb353
 F src/vdbeblob.c 5e61ce31aca17db8fb60395407457a8c1c7fb471dde405e0cd675974611dcfcd
 F src/vdbemem.c 316d518115f3720b4097f0231e2a3d6eefd06c787eccf44972f8d8f462153421
 F src/vdbesort.c 43756031ca7430f7aec3ef904824a7883c4ede783e51f280d99b9b65c0796e35
@@ -733,7 +733,7 @@ F src/vxworks.h d2988f4e5a61a4dfe82c6524dd3d6e4f2ce3cdb9
 F src/wal.c b9df133a705093da8977da5eb202eaadb844839f1c7297c08d33471f5491843d
 F src/wal.h c3aa7825bfa2fe0d85bef2db94655f99870a285778baa36307c0a16da32b226a
 F src/walker.c f890a3298418d7cba3b69b8803594fdc484ea241206a8dfa99db6dd36f8cbb3b
-F src/where.c d0d8e3cb2c11e77ba0f8f9ed8eada9d84dbd377167cdcf387b8eeb824c35a3ad
+F src/where.c 14ee8da18f9b4518af06931a32386dd0c7ec2eacab520726d6425e252e54b280
 F src/whereInt.h e25203e5bfee149f5f1225ae0166cfb4f1e65490c998a024249e98bb0647377c
 F src/wherecode.c 76bca3379219880d2527493b71a3be49e696f75396d3481e4de5d4ceec7886b2
 F src/whereexpr.c 7c5671a04b00c876bec5e99fd4e6f688065feb4773160fbf76fd7900d2901777
@@ -861,7 +861,7 @@ F test/cachespill.test 895997f84a25b323b166aecb69baab2d6380ea98f9e0bcc688c4493c5
 F test/capi2.test 4ee545824adc3eb33bf57ef89f77440b28188ec3da72e5425ff0fcdba32e8d5a
 F test/capi3.test 3910a73c38ac76d69778dd9eb481ab7cd6ed59117fc047b4f6056a5c72529de1
 F test/capi3b.test efb2b9cfd127efa84433cd7a2d72ce0454ae0dc4
-F test/capi3c.test 54e2dc0c8fd7c34ad1590d1be6864397da2438c95a9f5aee2f8fbc60c112e44b
+F test/capi3c.test 31d3a6778f2d06f2d9222bd7660c41a516d1518a059b069e96ebbeadb5a490f7
 F test/capi3d.test 8b778794af891b0dca3d900bd345fbc8ebd2aa2aae425a9dccdd10d5233dfbde
 F test/capi3e.test 3d49c01ef2a1a55f41d73cba2b23b5059ec460fe
 F test/carray01.test d55d57bf66b1af1c7ac55fae66ff4910884a8f5d21a90a18797ce386212a2634
@@ -2069,8 +2069,9 @@ F vsixtest/vsixtest.tcl 6a9a6ab600c25a91a7acc6293828957a386a8a93
 F vsixtest/vsixtest.vcxproj.data 2ed517e100c66dc455b492e1a33350c1b20fbcdc
 F vsixtest/vsixtest.vcxproj.filters 37e51ffedcdb064aad6ff33b6148725226cd608e
 F vsixtest/vsixtest_TemporaryKey.pfx e5b1b036facdb453873e7084e1cae9102ccc67a0
-P d149772d18c47bf986decb7e08d148b1d417bbcc8522fd6240ead836ec34074b
-R 46223eaf559523ff66a57b4bacb5c07e
-U dan
-Z 9e60d9184a671acda6ad686b21155410
+P c5d958eb942a8d6ea1e6e1d2d57637f9359d518965a28f298c7fbacdb9080f59 41b4c407b7f6968f4493fb9a0b220c55a6f6a353a8e6cb054efd3eb01bdd11dc
+R c48cc3fce2e639d8b7f17511d0860c6a
+T +closed 41b4c407b7f6968f4493fb9a0b220c55a6f6a353a8e6cb054efd3eb01bdd11dc
+U drh
+Z ce33d829c4c5aabbb58fbd24075e297a
 # Remove this line to create a well-formed Fossil manifest.
diff --git a/manifest.uuid b/manifest.uuid
index 6a306961ea..25ba762e5f 100644
--- a/manifest.uuid
+++ b/manifest.uuid
@@ -1 +1 @@
-c5d958eb942a8d6ea1e6e1d2d57637f9359d518965a28f298c7fbacdb9080f59
\ No newline at end of file
+bd8fa10e59f58886e10c84ea9934fa1b5f491aac2eff302757a76d2d36d59b69
\ No newline at end of file
diff --git a/src/select.c b/src/select.c
index 2288858ea7..d27bed026f 100644
--- a/src/select.c
+++ b/src/select.c
@@ -2211,7 +2211,7 @@ int sqlite3ColumnsFromExprList(
   *pnCol = nCol;
   *paCol = aCol;
 
-  for(i=0, pCol=aCol; i<nCol && !db->mallocFailed; i++, pCol++){
+  for(i=0, pCol=aCol; i<nCol && !pParse->nErr; i++, pCol++){
     struct ExprList_item *pX = &pEList->a[i];
     struct ExprList_item *pCollide;
     /* Get an appropriate name for the column
@@ -2261,7 +2261,10 @@ int sqlite3ColumnsFromExprList(
         if( zName[j]==':' ) nName = j;
       }
       zName = sqlite3MPrintf(db, "%.*z:%u", nName, zName, ++cnt);
-      if( cnt>3 ) sqlite3_randomness(sizeof(cnt), &cnt);
+      sqlite3ProgressCheck(pParse);
+      if( cnt>3 ){
+        sqlite3_randomness(sizeof(cnt), &cnt);
+      }
     }
     pCol->zCnName = zName;
     pCol->hName = sqlite3StrIHash(zName);
@@ -2274,14 +2277,14 @@ int sqlite3ColumnsFromExprList(
     }
   }
   sqlite3HashClear(&ht);
-  if( db->mallocFailed ){
+  if( pParse->nErr ){
     for(j=0; j<i; j++){
       sqlite3DbFree(db, aCol[j].zCnName);
     }
     sqlite3DbFree(db, aCol);
     *paCol = 0;
     *pnCol = 0;
-    return SQLITE_NOMEM_BKPT;
+    return pParse->rc;
   }
   return SQLITE_OK;
 }
@@ -2313,7 +2316,7 @@ void sqlite3SubqueryColumnTypes(
 
   assert( pSelect!=0 );
   assert( (pSelect->selFlags & SF_Resolved)!=0 );
-  assert( pTab->nCol==pSelect->pEList->nExpr || db->mallocFailed );
+  assert( pTab->nCol==pSelect->pEList->nExpr || pParse->nErr>0 );
   assert( aff==SQLITE_AFF_NONE || aff==SQLITE_AFF_BLOB );
   if( db->mallocFailed ) return;
   while( pSelect->pPrior ) pSelect = pSelect->pPrior;
diff --git a/src/sqlite.h.in b/src/sqlite.h.in
index 57bbdb7a1d..c6004f92db 100644
--- a/src/sqlite.h.in
+++ b/src/sqlite.h.in
@@ -3366,7 +3366,7 @@ int sqlite3_trace_v2(
 **
 ** ^The sqlite3_progress_handler(D,N,X,P) interface causes the callback
 ** function X to be invoked periodically during long running calls to
-** [sqlite3_exec()], [sqlite3_step()] and [sqlite3_get_table()] for
+** [sqlite3_step()] and [sqlite3_prepare()] and similar for
 ** database connection D.  An example use for this
 ** interface is to keep a GUI updated during a large query.
 **
@@ -3391,6 +3391,13 @@ int sqlite3_trace_v2(
 ** Note that [sqlite3_prepare_v2()] and [sqlite3_step()] both modify their
 ** database connections for the meaning of "modify" in this paragraph.
 **
+** The progress handler callback would originally only be invoked from the
+** bytecode engine.  It still might be invoked during [sqlite3_prepare()]
+** and similar because those routines might force a reparse of the schema
+** which involves running the bytecode engine.  However, beginning with
+** SQLite version 3.41.0, the progress handler callback might also be
+** invoked directly from [sqlite3_prepare()] while analyzing and generating
+** code for complex queries.
 */
 void sqlite3_progress_handler(sqlite3*, int, int(*)(void*), void*);
 
diff --git a/src/sqliteInt.h b/src/sqliteInt.h
index 09e8174066..3da5f13d5b 100644
--- a/src/sqliteInt.h
+++ b/src/sqliteInt.h
@@ -3754,6 +3754,9 @@ struct Parse {
   u32 nQueryLoop;      /* Est number of iterations of a query (10*log2(N)) */
   u32 oldmask;         /* Mask of old.* columns referenced */
   u32 newmask;         /* Mask of new.* columns referenced */
+#ifndef SQLITE_OMIT_PROGRESS_CALLBACK
+  u32 nProgressSteps;  /* xProgress steps taken during sqlite3_prepare() */
+#endif
   u8 eTriggerOp;       /* TK_UPDATE, TK_INSERT or TK_DELETE */
   u8 bReturning;       /* Coding a RETURNING trigger */
   u8 eOrconf;          /* Default ON CONFLICT policy for trigger steps */
@@ -4631,6 +4634,7 @@ char *sqlite3VMPrintf(sqlite3*,const char*, va_list);
 #endif
 
 void sqlite3SetString(char **, sqlite3*, const char*);
+void sqlite3ProgressCheck(Parse*);
 void sqlite3ErrorMsg(Parse*, const char*, ...);
 int sqlite3ErrorToParser(sqlite3*,int);
 void sqlite3Dequote(char*);
diff --git a/src/tclsqlite.c b/src/tclsqlite.c
index 4e25a65014..c455c29f14 100644
--- a/src/tclsqlite.c
+++ b/src/tclsqlite.c
@@ -3054,6 +3054,9 @@ deserialize_error:
       if( pDb->zProgress ){
         Tcl_AppendResult(interp, pDb->zProgress, (char*)0);
       }
+#ifndef SQLITE_OMIT_PROGRESS_CALLBACK
+      sqlite3_progress_handler(pDb->db, 0, 0, 0);
+#endif
     }else if( objc==4 ){
       char *zProgress;
       int len;
diff --git a/src/util.c b/src/util.c
index 23c6b1a66d..632d317e31 100644
--- a/src/util.c
+++ b/src/util.c
@@ -175,6 +175,26 @@ void sqlite3ErrorWithMsg(sqlite3 *db, int err_code, const char *zFormat, ...){
   }
 }
 
+/*
+** Check for interrupts and invoke progress callback.
+*/
+void sqlite3ProgressCheck(Parse *p){
+  sqlite3 *db = p->db;
+  if( AtomicLoad(&db->u1.isInterrupted) ){
+    p->nErr++;
+    p->rc = SQLITE_INTERRUPT;
+  }
+#ifndef SQLITE_OMIT_PROGRESS_CALLBACK
+  if( db->xProgress && (++p->nProgressSteps)>=db->nProgressOps ){
+    if( db->xProgress(db->pProgressArg) ){
+      p->nErr++;
+      p->rc = SQLITE_INTERRUPT;
+    }
+    p->nProgressSteps = 0;
+  }
+#endif
+}
+
 /*
 ** Add an error message to pParse->zErrMsg and increment pParse->nErr.
 **
diff --git a/src/vdbeaux.c b/src/vdbeaux.c
index ca9e5112a4..d04d8f1e17 100644
--- a/src/vdbeaux.c
+++ b/src/vdbeaux.c
@@ -574,6 +574,9 @@ static SQLITE_NOINLINE void resizeResolveLabel(Parse *p, Vdbe *v, int j){
     int i;
     for(i=p->nLabelAlloc; i<nNewSize; i++) p->aLabel[i] = -1;
 #endif
+    if( nNewSize>=100 && (nNewSize/100)>(p->nLabelAlloc/100) ){
+      sqlite3ProgressCheck(p);
+    }
     p->nLabelAlloc = nNewSize;
     p->aLabel[j] = v->nOp;
   }
diff --git a/src/where.c b/src/where.c
index 890c3bf52c..205f247621 100644
--- a/src/where.c
+++ b/src/where.c
@@ -2698,6 +2698,7 @@ static void whereLoopOutputAdjust(
       if( pX->iParent>=0 && (&pWC->a[pX->iParent])==pTerm ) break;
     }
     if( j<0 ){
+      sqlite3ProgressCheck(pWC->pWInfo->pParse);
       if( pLoop->maskSelf==pTerm->prereqAll ){
         /* If there are extra terms in the WHERE clause not used by an index
         ** that depend only on the table being scanned, and that will tend to
@@ -2865,7 +2866,10 @@ static int whereLoopAddBtreeIndex(
   WhereTerm *pTop = 0, *pBtm = 0; /* Top and bottom range constraints */
 
   pNew = pBuilder->pNew;
-  if( db->mallocFailed ) return SQLITE_NOMEM_BKPT;
+  assert( db->mallocFailed==0 || pParse->nErr>0 );
+  if( pParse->nErr ){
+    return pParse->rc;
+  }
   WHERETRACE(0x800, ("BEGIN %s.addBtreeIdx(%s), nEq=%d, nSkip=%d, rRun=%d\n",
                      pProbe->pTable->zName,pProbe->zName,
                      pNew->u.btree.nEq, pNew->nSkip, pNew->rRun));
@@ -3181,6 +3185,9 @@ static int whereLoopAddBtreeIndex(
      && (pNew->u.btree.nEq<pProbe->nKeyCol ||
            pProbe->idxType!=SQLITE_IDXTYPE_PRIMARYKEY)
     ){
+      if( pNew->u.btree.nEq>3 ){
+        sqlite3ProgressCheck(pParse);
+      }
       whereLoopAddBtreeIndex(pBuilder, pSrc, pProbe, nInMul+nIn);
     }
     pNew->nOut = saved_nOut;
@@ -4340,8 +4347,6 @@ static int whereLoopAddOr(
         if( rc==SQLITE_OK ){
           rc = whereLoopAddOr(&sSubBuild, mPrereq, mUnusable);
         }
-        assert( rc==SQLITE_OK || rc==SQLITE_DONE || sCur.n==0
-                || rc==SQLITE_NOMEM );
         testcase( rc==SQLITE_NOMEM && sCur.n>0 );
         testcase( rc==SQLITE_DONE );
         if( sCur.n==0 ){
diff --git a/test/capi3c.test b/test/capi3c.test
index 889ecbe859..247dbf35e5 100644
--- a/test/capi3c.test
+++ b/test/capi3c.test
@@ -1269,6 +1269,7 @@ ifcapable progress {
     sqlite3_finalize $STMT
   } {SQLITE_INTERRUPT}
   do_test capi3c-21.4 {
+    db progress
     set STMT [sqlite3_prepare $DB {SELECT * FROM t3} -1 TAIL]
     db progress 5 "expr 1"
     sqlite3_step $STMT