diff --git a/modules/core/shared/src/main/scala-3/syntax/StringContextOps.scala b/modules/core/shared/src/main/scala-3/syntax/StringContextOps.scala
index 235279b43..7567d6296 100644
--- a/modules/core/shared/src/main/scala-3/syntax/StringContextOps.scala
+++ b/modules/core/shared/src/main/scala-3/syntax/StringContextOps.scala
@@ -49,7 +49,7 @@ object StringContextOps {
 
   def yell(s: String) = println(s"${Console.RED}$s${Console.RESET}")
 
-  def sqlImpl(sc: Expr[StringContext], argsExpr: Expr[Seq[Any]])(using qc:Quotes): Expr[Any] = {
+  def sqlImpl(sc: Expr[StringContext], argsExpr: Expr[Seq[Any]])(using qc: Quotes): Expr[Any] = {
     import qc.reflect.report
 
     // Ok we want to construct an Origin here
@@ -78,23 +78,17 @@ object StringContextOps {
     val partsEncoders: Either[Expr[Any], (List[Expr[Part]], List[Expr[Any]])] = strings.flatMap { strings =>
       val lastPart: Expr[Part] = '{Str(${Expr(strings.last)})}
       (strings zip args).reverse.foldLeftM((List[Expr[Part]](lastPart), List.empty[Expr[Any]])) {
-
         case ((parts, es), (str, arg)) =>
-
-          if (str.endsWith("#")) {
-
+          if (str.endsWith("#")) then {
             // Interpolations like "...#$foo ..." require `foo` to be a String.
             arg match {
               case '{ $s: String } => Right(('{Str(${Expr(str.dropRight(1))})} :: '{Str($s)} :: parts, es))
               case '{ $a: t }     =>
-              report.error(s"Found ${Type.show[t]}, expected String.}", a)
-              Left('{ compiletime.error("Expected String") }) ///
-          }
-
+                report.error(s"Found ${Type.show[t]}, expected String.}", a)
+                Left('{ compiletime.error("Expected String") }) ///
+            }
           } else {
-
             arg match {
-
               // The interpolated thing is an Encoder.
               case '{ $e: Encoder[t] } =>
                 val newParts    = '{Str(${Expr(str)})} :: '{Par($e.sql)} :: parts
@@ -113,13 +107,10 @@ object StringContextOps {
                 Right((newParts, newEncoders))
 
               case '{ $a: t } =>
-              report.error(s"Found ${Type.show[t]}, expected String, Encoder, or Fragment.", a)
-              Left('{compiletime.error("Expected String, Encoder, or Fragment.")})
-
+                report.error(s"Found ${Type.show[t]}, expected String, Encoder, or Fragment.", a)
+                Left('{compiletime.error("Expected String, Encoder, or Fragment.")})
             }
-
           }
-
       }
     }
 
@@ -127,18 +118,22 @@ object StringContextOps {
     partsEncoders.map { (parts, encoders) =>
       val finalEnc: Expr[Any] =
         if encoders.isEmpty then '{ Void.codec }
-        else if legacyCommandSyntax then encoders.reduceLeft {
-          case ('{$a : Encoder[a]}, '{ $b : Encoder[b] }) => '{$a ~ $b}
-        } else encoders.reduceRight {
-          case ('{$a : Encoder[a]}, '{ $b : Encoder[bh *: bt] }) => '{$a *: $b}
-          case ('{$a : Encoder[a]}, '{ $b : Encoder[b] }) => '{$a *: $b}
+        else if legacyCommandSyntax then
+          encoders.reduceLeft {
+            case ('{$a : Encoder[a]}, '{ $b : Encoder[b] }) => '{$a ~ $b}
+          }
+        else if encoders.size == 1 then encoders.head
+        else {
+          val last: Expr[Any] = encoders.last match {
+            case '{$a: Encoder[a]} => '{$a.imap(_ *: EmptyTuple)(_.head)}
+          }
+          encoders.init.foldRight(last) { case ('{$a: Encoder[a]}, '{$acc: Encoder[t & Tuple]}) => '{$a *: $acc} }
         }
 
       finalEnc match {
         case '{ $e : Encoder[t] } => '{ fragmentFromParts[t](${Expr.ofList(parts)}, $e, $origin) }
       }
     }.merge
-
   }
 
   def idImpl(sc: Expr[StringContext])(using qc: Quotes): Expr[Identifier] =
diff --git a/modules/tests/shared/src/test/scala/issue/990.scala b/modules/tests/shared/src/test/scala/issue/990.scala
new file mode 100644
index 000000000..d73c9b56a
--- /dev/null
+++ b/modules/tests/shared/src/test/scala/issue/990.scala
@@ -0,0 +1,15 @@
+// Copyright (c) 2018-2021 by Rob Norris
+// This software is licensed under the MIT License (MIT).
+// For more information see LICENSE or https://opensource.org/licenses/MIT
+
+package tests.issue
+
+import skunk._
+import skunk.codec.all._
+import skunk.syntax.all._
+
+
+object Issue990 {
+  def updateBy[A](where: Fragment[A]): Command[String *: A *: EmptyTuple] =
+    sql"""UPDATE foo SET bar = $text WHERE $where;""".command
+}