diff --git a/modules/query/src/main/scala/docspell/query/ItemQueryParser.scala b/modules/query/src/main/scala/docspell/query/ItemQueryParser.scala
index cea6c09e..cf9b491c 100644
--- a/modules/query/src/main/scala/docspell/query/ItemQueryParser.scala
+++ b/modules/query/src/main/scala/docspell/query/ItemQueryParser.scala
@@ -9,17 +9,18 @@ import docspell.query.internal.ExprUtil
 object ItemQueryParser {
 
   @JSExport
-  def parse(input: String): Either[String, ItemQuery] =
+  def parse(input: String): Either[ParseFailure, ItemQuery] =
     if (input.isEmpty) Right(ItemQuery.all)
     else {
       val in = if (input.charAt(0) == '(') input else s"(& $input )"
       ExprParser
         .parseQuery(in)
         .left
-        .map(pe => s"Error parsing: '$input': $pe") //TODO
+        .map(ParseFailure.fromError(in))
         .map(q => q.copy(expr = ExprUtil.reduce(q.expr)))
     }
 
   def parseUnsafe(input: String): ItemQuery =
-    parse(input).fold(sys.error, identity)
+    parse(input).fold(m => sys.error(m.render), identity)
+
 }
diff --git a/modules/query/src/main/scala/docspell/query/ParseFailure.scala b/modules/query/src/main/scala/docspell/query/ParseFailure.scala
new file mode 100644
index 00000000..05235c03
--- /dev/null
+++ b/modules/query/src/main/scala/docspell/query/ParseFailure.scala
@@ -0,0 +1,65 @@
+package docspell.query
+
+import cats.data.{NonEmptyList => Nel}
+import cats.parse.Parser
+import cats.parse.Parser.Expectation.EndOfString
+import cats.parse.Parser.Expectation.ExpectedFailureAt
+import cats.parse.Parser.Expectation.Fail
+import cats.parse.Parser.Expectation.FailWith
+import cats.parse.Parser.Expectation.InRange
+import cats.parse.Parser.Expectation.Length
+import cats.parse.Parser.Expectation.OneOfStr
+import cats.parse.Parser.Expectation.StartOfString
+
+final case class ParseFailure(
+    input: String,
+    failedAt: Int,
+    messages: Nel[ParseFailure.Message]
+) {
+
+  def render: String = {
+    val items = messages.map(_.msg).toList.mkString(", ")
+    s"Failed to read input near $failedAt: $input\nDetails: $items"
+  }
+}
+
+object ParseFailure {
+
+  final case class Message(offset: Int, msg: String)
+
+  private[query] def fromError(input: String)(pe: Parser.Error): ParseFailure =
+    ParseFailure(
+      input,
+      pe.failedAtOffset,
+      Parser.Expectation.unify(pe.expected).map(expectationToMsg)
+    )
+
+  private[query] def expectationToMsg(e: Parser.Expectation): Message =
+    e match {
+      case StartOfString(offset) =>
+        Message(offset, "Expected start of string")
+
+      case FailWith(offset, message) =>
+        Message(offset, message)
+
+      case InRange(offset, lower, upper) =>
+        if (lower == upper) Message(offset, s"Expected character: $lower")
+        else Message(offset, s"Expected character from range: [$lower .. $upper]")
+
+      case Length(offset, expected, actual) =>
+        Message(offset, s"Expected input of length $expected, but got $actual")
+
+      case ExpectedFailureAt(offset, matched) =>
+        Message(offset, s"Expected failing, but matched '$matched'")
+
+      case EndOfString(offset, length) =>
+        Message(offset, s"Expected end of string at length: $length")
+
+      case Fail(offset) =>
+        Message(offset, s"Failed to parse near $offset")
+
+      case OneOfStr(offset, strs) =>
+        val options = strs.mkString(", ")
+        Message(offset, s"Expected one of the following strings: $options")
+    }
+}
diff --git a/modules/restserver/src/main/scala/docspell/restserver/routes/ItemRoutes.scala b/modules/restserver/src/main/scala/docspell/restserver/routes/ItemRoutes.scala
index 510273a0..e93e4e95 100644
--- a/modules/restserver/src/main/scala/docspell/restserver/routes/ItemRoutes.scala
+++ b/modules/restserver/src/main/scala/docspell/restserver/routes/ItemRoutes.scala
@@ -61,7 +61,7 @@ object ItemRoutes {
         val of = offset.getOrElse(0)
         query match {
           case Left(err) =>
-            BadRequest(BasicResult(false, err))
+            BadRequest(BasicResult(false, err.render))
           case Right(sq) =>
             for {
               items <- backend.itemSearch.findItems(cfg.maxNoteLength)(