Index: src/shell_indexes.c
==================================================================
--- src/shell_indexes.c
+++ src/shell_indexes.c
@@ -32,10 +32,11 @@
   char *zColl;                    /* Collation sequence */
   int bRange;                     /* True for range, false for eq */
   int iCol;                       /* Constrained table column */
   i64 depmask;                    /* Dependency mask */
   int bFlag;                      /* Used by idxFindCompatible() */
+  int bDesc;                      /* True if ORDER BY <expr> DESC */
   IdxConstraint *pNext;           /* Next constraint in pEq or pRange list */
   IdxConstraint *pLink;           /* See above */
 };
 
 /*
@@ -196,15 +197,21 @@
         break;
       }
 
       case SQLITE_WHEREINFO_ORDERBY: {
         IdxConstraint *pNew = idxNewConstraint(&p->rc, zVal);
-        IdxConstraint **pp;
         if( pNew==0 ) return;
         pNew->iCol = iVal;
-        for(pp=&p->pScan->pOrder; *pp; pp=&(*pp)->pNext);
-        *pp = pNew;
+        pNew->bDesc = (int)mask;
+        if( p->pScan->pOrder==0 ){
+          p->pScan->pOrder = pNew;
+        }else{
+          IdxConstraint *pIter;
+          for(pIter=p->pScan->pOrder; pIter->pNext; pIter=pIter->pNext);
+          pIter->pNext = pNew;
+          pIter->pLink = pNew;
+        }
         break;
       }
 
       case SQLITE_WHEREINFO_EQUALS:
       case SQLITE_WHEREINFO_RANGE: {
@@ -506,10 +513,14 @@
       zRet = idxAppendText(pRc, zRet, " COLLATE %Q", pCons->zColl);
     }else{
       zRet = idxAppendText(pRc, zRet, " COLLATE %s", pCons->zColl);
     }
   }
+
+  if( pCons->bDesc ){
+    zRet = idxAppendText(pRc, zRet, " DESC");
+  }
   return zRet;
 }
 
 /*
 ** Search database dbm for an index compatible with the one idxCreateFromCons()
@@ -810,11 +821,13 @@
       }else if( memcmp(&zDetail[i], " USING COVERING INDEX ", 22)==0 ){
         zIdx = &zDetail[i+22];
       }
       if( zIdx ){
         int nIdx = 0;
-        while( zIdx[nIdx]!='\0' && zIdx[nIdx]!=' ' ) nIdx++;
+        while( zIdx[nIdx]!='\0' && (zIdx[nIdx]!=' ' || zIdx[nIdx+1]!='(') ){
+          nIdx++;
+        }
         sqlite3_bind_text(pSelect, 1, zIdx, nIdx, SQLITE_STATIC);
         if( SQLITE_ROW==sqlite3_step(pSelect) ){
           i64 iRowid = sqlite3_column_int64(pSelect, 0);
           const char *zSql = (const char*)sqlite3_column_text(pSelect, 1);
           if( iRowid>=pCtx->iIdxRowid ){

Index: src/where.c
==================================================================
--- src/where.c
+++ src/where.c
@@ -3988,15 +3988,17 @@
           int i;
           int bFirst = 1;
           for(i=0; i<p->pOrderBy->nExpr; i++){
             Expr *pExpr = p->pOrderBy->a[i].pExpr; 
             CollSeq *pColl = sqlite3ExprCollSeq(pParse, pExpr);
+            assert( pColl || pParse->rc );
             pExpr = sqlite3ExprSkipCollate(pExpr);
             if( pExpr->op==TK_COLUMN && pExpr->iTable==pItem->iCursor ){
               int iCol = pExpr->iColumn;
-              if( iCol>=0 ){
-                x(pCtx, SQLITE_WHEREINFO_ORDERBY, pColl->zName, iCol, 0); 
+              if( pColl && iCol>=0 ){
+                int bDesc = p->pOrderBy->a[i].sortOrder;
+                x(pCtx, SQLITE_WHEREINFO_ORDERBY, pColl->zName, iCol, bDesc); 
               }
             }
           }
         }
 

ADDED   test/shell6.test
Index: test/shell6.test
==================================================================
--- /dev/null
+++ test/shell6.test
@@ -0,0 +1,191 @@
+# 2009 Nov 11
+#
+# 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.
+#
+#***********************************************************************
+#
+# The focus of this file is testing the CLI shell tool. Specifically,
+# the ".recommend" command.
+#
+#
+
+# Test plan:
+#
+#   shell1-1.*: Basic command line option handling.
+#   shell1-2.*: Basic "dot" command token parsing.
+#   shell1-3.*: Basic test that "dot" command can be called.
+#
+set testdir [file dirname $argv0]
+source $testdir/tester.tcl
+set testprefix shell6
+
+if {$tcl_platform(platform)=="windows"} {
+  set CLI "sqlite3.exe"
+} else {
+  set CLI "./sqlite3"
+}
+if {![file executable $CLI]} {
+  finish_test
+  return
+}
+
+
+proc squish {txt} {
+  regsub -all {[[:space:]]+} $txt { }
+}
+
+proc do_rec_test {tn sql res} {
+  set res [squish [string trim $res]]
+  set tst [subst -nocommands { 
+    squish [lindex [catchcmd [list -rec test.db {$sql;}]] 1]
+  }]
+  uplevel [list do_test $tn $tst $res]
+}
+
+proc do_setup_rec_test {tn setup sql res} {
+  reset_db
+  db eval $setup
+  uplevel [list do_rec_test $tn $sql $res]
+}
+
+
+do_setup_rec_test 1.1 { CREATE TABLE t1(a, b, c) } {
+  SELECT * FROM t1
+} {
+  (no new indexes)
+  0|0|0|SCAN TABLE t1
+}
+
+do_setup_rec_test 1.2 {
+  CREATE TABLE t1(a, b, c);
+} {
+  SELECT * FROM t1 WHERE b>?;
+} {
+  CREATE INDEX t1_idx_00000062 ON t1(b) 
+  0|0|0|SEARCH TABLE t1 USING INDEX t1_idx_00000062 (b>?)
+}
+
+do_setup_rec_test 1.3 {
+  CREATE TABLE t1(a, b, c);
+} {
+  SELECT * FROM t1 WHERE b COLLATE nocase BETWEEN ? AND ?
+} {
+  CREATE INDEX t1_idx_3e094c27 ON t1(b COLLATE NOCASE) 
+  0|0|0|SEARCH TABLE t1 USING INDEX t1_idx_3e094c27 (b>? AND b<?)
+}
+
+do_setup_rec_test 1.4 {
+  CREATE TABLE t1(a, b, c);
+} {
+  SELECT a FROM t1 ORDER BY b;
+} {
+  CREATE INDEX t1_idx_00000062 ON t1(b) 
+  0|0|0|SCAN TABLE t1 USING INDEX t1_idx_00000062
+}
+
+do_setup_rec_test 1.5 {
+  CREATE TABLE t1(a, b, c);
+} {
+  SELECT a FROM t1 WHERE a=? ORDER BY b;
+} {
+  CREATE INDEX t1_idx_000123a7 ON t1(a, b) 
+  0|0|0|SEARCH TABLE t1 USING COVERING INDEX t1_idx_000123a7 (a=?)
+}
+
+do_setup_rec_test 1.6 {
+  CREATE TABLE t1(a, b, c);
+} {
+  SELECT min(a) FROM t1
+} {
+  CREATE INDEX t1_idx_00000061 ON t1(a) 
+  0|0|0|SEARCH TABLE t1 USING COVERING INDEX t1_idx_00000061
+}
+
+do_setup_rec_test 1.7 {
+  CREATE TABLE t1(a, b, c);
+} {
+  SELECT * FROM t1 ORDER BY a, b, c;
+} {
+  CREATE INDEX t1_idx_033e95fe ON t1(a, b, c) 
+  0|0|0|SCAN TABLE t1 USING COVERING INDEX t1_idx_033e95fe
+}
+
+do_setup_rec_test 1.8 {
+  CREATE TABLE t1(a, b, c);
+} {
+  SELECT * FROM t1 ORDER BY a ASC, b COLLATE nocase DESC, c ASC;
+} {
+  CREATE INDEX t1_idx_5be6e222 ON t1(a, b COLLATE NOCASE DESC, c)
+  0|0|0|SCAN TABLE t1 USING COVERING INDEX t1_idx_5be6e222
+}
+
+do_setup_rec_test 1.9 {
+  CREATE TABLE t1(a COLLATE NOCase, b, c);
+} {
+  SELECT * FROM t1 WHERE a=?
+} {
+  CREATE INDEX t1_idx_00000061 ON t1(a) 
+  0|0|0|SEARCH TABLE t1 USING INDEX t1_idx_00000061 (a=?)
+}
+
+
+# Tables with names that require quotes.
+#
+do_setup_rec_test 8.1 {
+  CREATE TABLE "t t"(a, b, c);
+} {
+  SELECT * FROM "t t" WHERE a=?
+} {
+  CREATE INDEX 't t_idx_00000061' ON 't t'(a)
+  0|0|0|SEARCH TABLE t t USING INDEX t t_idx_00000061 (a=?) 
+}
+
+do_setup_rec_test 8.2 {
+  CREATE TABLE "t t"(a, b, c);
+} {
+  SELECT * FROM "t t" WHERE b BETWEEN ? AND ?
+} {
+  CREATE INDEX 't t_idx_00000062' ON 't t'(b) 
+  0|0|0|SEARCH TABLE t t USING INDEX t t_idx_00000062 (b>? AND b<?)
+}
+
+# Columns with names that require quotes.
+#
+do_setup_rec_test 9.1 {
+  CREATE TABLE t3(a, "b b", c);
+} {
+  SELECT * FROM t3 WHERE "b b" = ?
+} {
+  CREATE INDEX t3_idx_00050c52 ON t3('b b') 
+  0|0|0|SEARCH TABLE t3 USING INDEX t3_idx_00050c52 (b b=?)
+}
+
+do_setup_rec_test 9.2 {
+  CREATE TABLE t3(a, "b b", c);
+} {
+  SELECT * FROM t3 ORDER BY "b b"
+} {
+  CREATE INDEX t3_idx_00050c52 ON t3('b b') 
+  0|0|0|SCAN TABLE t3 USING INDEX t3_idx_00050c52
+}
+
+# Transitive constraints
+#
+do_setup_rec_test 10.1 {
+  CREATE TABLE t5(a, b);
+  CREATE TABLE t6(c, d);
+} {
+  SELECT * FROM t5, t6 WHERE a=? AND b=c AND c=?
+} {
+  CREATE INDEX t6_idx_00000063 ON t6(c) 
+  CREATE INDEX t5_idx_000123a7 ON t5(a, b) 
+  0|0|1|SEARCH TABLE t6 USING INDEX t6_idx_00000063 (c=?) 
+  0|1|0|SEARCH TABLE t5 USING COVERING INDEX t5_idx_000123a7 (a=? AND b=?)
+}
+
+finish_test