diff --git a/build.sbt b/build.sbt
index 85c59512d6..98fcbaa14e 100644
--- a/build.sbt
+++ b/build.sbt
@@ -22,7 +22,8 @@ lazy val commonSettings = Seq(
         Seq("-Ywarn-unused:_,imports", "-Ywarn-unused:imports", "-release", "8")
       case Some((2, 11)) =>
         Seq()
-      case _ => sys.error("Unsupported scala version")
+      case _ => sys.error("""The Scala version you are using is not supported. Please use a supported version of Scala.
+      |For more details, visit our Scala version compatibility guide.""".stripMargin.replaceAll("\n", " "))
     }
   },
   javacOptions ++= javacReleaseOption,
diff --git a/core/js/src/main/scala/sigma/crypto/Platform.scala b/core/js/src/main/scala/sigma/crypto/Platform.scala
index 88001ba140..8424ba935b 100644
--- a/core/js/src/main/scala/sigma/crypto/Platform.scala
+++ b/core/js/src/main/scala/sigma/crypto/Platform.scala
@@ -246,7 +246,9 @@ object Platform {
     case c: Coll[_] => tpe match {
       case STuple(items) => c.tItem == sigma.AnyType && c.length == items.length
       case tpeColl: SCollection[_] => true
-      case _ => sys.error(s"Collection value $c has unexpected type $tpe")
+      case _ => sys.error(s"""The collection value $c has an unexpected type: $tpe.
+      |Please ensure the value is of the expected type.
+      |For more details, refer to our type compatibility guide.""".stripMargin.replaceAll("\n", " "))
     }
     case _: Option[_] => tpe.isOption
     case _: Tuple2[_, _] => tpe.isTuple && tpe.asTuple.items.length == 2
diff --git a/core/js/src/main/scala/sigma/reflection/Platform.scala b/core/js/src/main/scala/sigma/reflection/Platform.scala
index 199729fc7a..8a33c32d06 100644
--- a/core/js/src/main/scala/sigma/reflection/Platform.scala
+++ b/core/js/src/main/scala/sigma/reflection/Platform.scala
@@ -19,7 +19,9 @@ object Platform {
         assert(c.clazz == clazz)
         c
       case _ =>
-        sys.error(s"Cannot find RClass data for $clazz")
+        sys.error(s"""We couldn't find the RClass data for $clazz.
+        |Please verify that the class name is correct and try again.
+        |For further assistance, visit our RClass data documentation.""".stripMargin.replaceAll("\n", " "))
       // Uncomment the following line to collect missing reflection data and generate Scala code for it
       //        memoize(classes)(clazz, new JRClass[T](clazz))
     }
diff --git a/core/jvm/src/main/scala/sigma/crypto/Platform.scala b/core/jvm/src/main/scala/sigma/crypto/Platform.scala
index b71694e81b..013269f382 100644
--- a/core/jvm/src/main/scala/sigma/crypto/Platform.scala
+++ b/core/jvm/src/main/scala/sigma/crypto/Platform.scala
@@ -175,7 +175,9 @@ object Platform {
     case c: Coll[_] => tpe match {
       case STuple(items) => c.tItem == sigma.AnyType && c.length == items.length
       case _: SCollection[_] => true
-      case _ => sys.error(s"Collection value $c has unexpected type $tpe")
+      case _ => sys.error(s"""The collection value $c has an unexpected type: $tpe.
+                            |Please ensure the value is of the expected type.
+                            |For more details, refer to our type compatibility guide.""".stripMargin.replaceAll("\n", " "))
     }
     case _: Option[_] => tpe.isOption
     case _: Tuple2[_, _] => tpe.isTuple && tpe.asTuple.items.length == 2
diff --git a/core/shared/src/main/scala/sigma/Evaluation.scala b/core/shared/src/main/scala/sigma/Evaluation.scala
index d86b7c1650..25d9bc7ff6 100644
--- a/core/shared/src/main/scala/sigma/Evaluation.scala
+++ b/core/shared/src/main/scala/sigma/Evaluation.scala
@@ -51,7 +51,8 @@ object Evaluation {
       val tpeArg = args(0)
       funcRType(stypeToRType(tpeArg), stypeToRType(tpeRange))
     case _ =>
-      sys.error(s"Don't know how to convert SType $t to RType")
+      sys.error(s"""We couldn't convert SType $t to RType. Please ensure that $t is compatible with RType.
+      |For detailed guidance, visit our type conversion documentation.""".stripMargin.replaceAll("\n", " "))
   }).asInstanceOf[RType[T#WrappedType]]
 
   /** Transforms RType descriptor of SigmaDsl, which is used during evaluation,
@@ -82,7 +83,8 @@ object Evaluation {
     case ct: CollType[_] => SCollection(rtypeToSType(ct.tItem))
     case ft: FuncType[_,_] => SFunc(rtypeToSType(ft.tDom), rtypeToSType(ft.tRange))
     case pt: PairType[_,_] => STuple(rtypeToSType(pt.tFst), rtypeToSType(pt.tSnd))
-    case _ => sys.error(s"Don't know how to convert RType $t to SType")
+    case _ => sys.error(s"""We couldn't convert SType $t to RType. Please ensure that $t is compatible with RType.
+              |For detailed guidance, visit our type conversion documentation.""".stripMargin.replaceAll("\n", " "))
   }
 
   /** Convert SigmaDsl representation of tuple to ErgoTree serializable representation. */
@@ -90,7 +92,9 @@ object Evaluation {
     case t: Tuple2[_,_] => TupleColl(t._1, t._2)
     case a: Coll[Any]@unchecked if a.tItem == sigma.AnyType => a
     case _ =>
-      sys.error(s"Cannot execute fromDslTuple($value, $tupleTpe)")
+      sys.error(s"""Execution failed for fromDslTuple with value $value and type $tupleTpe.
+      |Please ensure the value matches the expected tuple type.
+      |For more details, refer to our DSL tuple documentation.""".stripMargin.replaceAll("\n", " "))
   }
 
   /** Convert ErgoTree serializable representation of tuple to SigmaDsl representation. */
diff --git a/core/shared/src/main/scala/sigma/ast/SType.scala b/core/shared/src/main/scala/sigma/ast/SType.scala
index f75cbc9e8b..c9a43d859d 100644
--- a/core/shared/src/main/scala/sigma/ast/SType.scala
+++ b/core/shared/src/main/scala/sigma/ast/SType.scala
@@ -163,17 +163,21 @@ object SType {
     case _: SOption[_] => x.isInstanceOf[Option[_]]
     case t: STuple =>
       if (t.items.length == 2) x.isInstanceOf[Tuple2[_,_]]
-      else sys.error(s"Unsupported tuple type $t")
+      else sys.error(s"""The tuple type $t is not supported.
+      |Please ensure you are using a compatible tuple type.
+      |For further assistance, consult our tuple type documentation.""".stripMargin.replaceAll("\n", " "))
     case tF: SFunc =>
       if (tF.tDom.length == 1) x.isInstanceOf[Function1[_,_]]
-      else sys.error(s"Unsupported function type $tF")
+      else sys.error(s"""The function type $tF is not supported. Please ensure you are using a compatible function type.
+      |For more details, refer to our function type documentation.""".stripMargin.replaceAll("\n", " "))
     case SContext => x.isInstanceOf[Context]
     case SAvlTree => x.isInstanceOf[AvlTree]
     case SGlobal => x.isInstanceOf[SigmaDslBuilder]
     case SHeader => x.isInstanceOf[Header]
     case SPreHeader => x.isInstanceOf[PreHeader]
     case SUnit => x.isInstanceOf[Unit]
-    case _ => sys.error(s"Unknown type $tpe")
+    case _ => sys.error(s"""The type $tpe is unknown. Please verify the type and ensure it is correctly defined.
+    |For further assistance, consult our type definition documentation.""".stripMargin.replaceAll("\n", " "))
   }
 
 
@@ -346,7 +350,9 @@ object SNumericType extends STypeCompanion {
   override def typeId: TypeCode = 106: Byte
 
   /** Since this object is not used in SMethod instances. */
-  override def reprClass: RClass[_] = sys.error(s"Shouldn't be called.")
+  override def reprClass: RClass[_] = sys.error("""The reprClass method should not be invoked.
+      |Please review the documentation for correct usage.
+      |For more information, refer to our reprClass documentation.""".stripMargin.replaceAll("\n", " "))
 }
 
 /** Descriptor of ErgoTree type `Boolean` holding `true` or `false` values. */
@@ -368,14 +374,18 @@ case object SByte extends SPrimType with SEmbeddable with SNumericType with SMon
   override def numericTypeIndex: Int = 0
   override def upcast(v: AnyVal): Byte = v match {
     case b: Byte => b
-    case _ => sys.error(s"Cannot upcast value $v to the type $this")
+    case _ => sys.error(s"""Unable to upcast value $v to type $this.
+    |Please ensure compatibility between the value and the expected type.
+    |For more guidance, refer to our type casting documentation.""".stripMargin.replaceAll("\n", " "))
   }
   override def downcast(v: AnyVal): Byte = v match {
     case b: Byte => b
     case s: Short => s.toByteExact
     case i: Int => i.toByteExact
     case l: Long => l.toByteExact
-    case _ => sys.error(s"Cannot downcast value $v to the type $this")
+    case _ => sys.error(s"""Unable to downcast value $v to type $this.
+                         |Please ensure compatibility between the value and the expected type.
+                         |For more guidance, refer to our type casting documentation.""".stripMargin.replaceAll("\n", " "))
   }
 }
 
diff --git a/core/shared/src/main/scala/sigma/data/CSigmaProp.scala b/core/shared/src/main/scala/sigma/data/CSigmaProp.scala
index d8a472424c..924fd75b24 100644
--- a/core/shared/src/main/scala/sigma/data/CSigmaProp.scala
+++ b/core/shared/src/main/scala/sigma/data/CSigmaProp.scala
@@ -15,7 +15,9 @@ case class CSigmaProp(sigmaTree: SigmaBoolean) extends SigmaProp with WrapperOf[
   // TODO refactor: remove this (it shouldn't be used in interpreter)
   override def isValid: Boolean = sigmaTree match {
     case p: TrivialProp => p.condition
-    case _ => sys.error(s"Method CostingSigmaProp.isValid is not defined for $sigmaTree")
+    case _ => sys.error(s"""The method CostingSigmaProp.isValid is not defined for the $sigmaTree.
+         |Please ensure you are using the correct method for $sigmaTree.
+         |For further details, refer to our CostingSigmaProp documentation.""".stripMargin.replaceAll("\n", " "))
   }
 
   override def propBytes: Coll[Byte] = {
diff --git a/core/shared/src/main/scala/sigma/serialization/CoreDataSerializer.scala b/core/shared/src/main/scala/sigma/serialization/CoreDataSerializer.scala
index b4b20feb4c..39760fcd25 100644
--- a/core/shared/src/main/scala/sigma/serialization/CoreDataSerializer.scala
+++ b/core/shared/src/main/scala/sigma/serialization/CoreDataSerializer.scala
@@ -63,7 +63,9 @@ class CoreDataSerializer {
       val len = arr.length
       assert(arr.length == t.items.length, s"Type $t doesn't correspond to value $arr")
       if (len > 0xFFFF)
-        sys.error(s"Length of tuple ${arr.length} exceeds ${0xFFFF} limit.")
+        sys.error(s"""The tuple length (${arr.length}) exceeds the maximum limit (${0xFFFF}).
+             |Please reduce the tuple size to meet the limit.
+             |For more details, refer to our tuple length documentation.""".stripMargin.replaceAll("\n", " "))
       var i = 0
       while (i < arr.length) {
         serialize[SType](arr(i), t.items(i), w)
diff --git a/core/shared/src/main/scala/sigma/serialization/TypeSerializer.scala b/core/shared/src/main/scala/sigma/serialization/TypeSerializer.scala
index 9c84de0944..ac460feefd 100644
--- a/core/shared/src/main/scala/sigma/serialization/TypeSerializer.scala
+++ b/core/shared/src/main/scala/sigma/serialization/TypeSerializer.scala
@@ -85,7 +85,10 @@ class TypeSerializer {
         serialize(t2, w)
     }
     case STuple(items) if items.length < 2 =>
-      sys.error(s"Invalid Tuple type with less than 2 items $items")
+      sys.error(
+        s"""The Tuple type with less than 2 items ($items) is invalid.
+           |Please ensure tuples have at least 2 items for proper functionality.
+           |For guidance, refer to our Tuple type documentation.""".stripMargin.replaceAll("\n", " "))
     case tup: STuple => tup.items.length match {
       case 3 =>
         // Triple of types
diff --git a/data/shared/src/main/scala/org/ergoplatform/ErgoBoxCandidate.scala b/data/shared/src/main/scala/org/ergoplatform/ErgoBoxCandidate.scala
index ba306159d4..d97b119aad 100644
--- a/data/shared/src/main/scala/org/ergoplatform/ErgoBoxCandidate.scala
+++ b/data/shared/src/main/scala/org/ergoplatform/ErgoBoxCandidate.scala
@@ -151,7 +151,9 @@ object ErgoBoxCandidate {
         val amount = amounts(i)
         if (tokensInTx.isDefined) {
           val tokenIndex = tokensInTx.get.indexWhere(_ == id, 0) // using equality on Coll
-          if (tokenIndex == -1) sys.error(s"failed to find token id ($id) in tx's digest index")
+          if (tokenIndex == -1) sys.error(s"""Failed to locate token ID ($id) in the transaction's digest index.
+               |Please verify the token ID and try again.
+               |For further assistance, consult our transaction documentation.""".stripMargin.replaceAll("\n", " "))
           w.putUInt(tokenIndex)
         } else {
           w.putBytes(id.toArray)
@@ -161,7 +163,10 @@ object ErgoBoxCandidate {
 
       val nRegs = box.additionalRegisters.keys.size
       if (nRegs + ErgoBox.startingNonMandatoryIndex > 255)
-        sys.error(s"The number of non-mandatory indexes $nRegs exceeds ${255 - ErgoBox.startingNonMandatoryIndex} limit.")
+        sys.error(
+          s"""The number of non-mandatory indexes ($nRegs) exceeds the maximum limit (${255 - ErgoBox.startingNonMandatoryIndex}).
+             |Please reduce the number of non-mandatory indexes to meet the limit.
+             |For more details, refer to our indexing documentation.""".stripMargin.replaceAll("\n", " "))
       w.putUByte(nRegs)
       // we assume non-mandatory indexes are densely packed from startingNonMandatoryIndex
       // this convention allows to save 1 bite for each register
@@ -173,8 +178,10 @@ object ErgoBoxCandidate {
           case Some(v) =>
             w.putValue(v)
           case None =>
-            sys.error(s"Set of non-mandatory indexes is not densely packed: " +
-              s"register R$regId is missing in the range [$startReg .. $endReg]")
+            sys.error(s"""The set of non-mandatory indexes is not densely packed:
+                 |register R$regId is missing in the range [$startReg .. $endReg].
+                 |Please ensure all registers in this range are sequentially filled.
+                 |For more information, refer to our register packing guidelines.""".stripMargin.replaceAll("\n", " "))
         }
       }
     }
diff --git a/data/shared/src/main/scala/sigma/ast/syntax.scala b/data/shared/src/main/scala/sigma/ast/syntax.scala
index 5a257481cb..dff7fecbf5 100644
--- a/data/shared/src/main/scala/sigma/ast/syntax.scala
+++ b/data/shared/src/main/scala/sigma/ast/syntax.scala
@@ -58,7 +58,10 @@ object syntax {
     def length: Int = matchCase(_.items.length, _.value.length, _.items.length)
 
     /** Returns a sequence of items in the collection expression. */
-    def items: Seq[Value[SType]] = matchCase(_.items, _ => sys.error(s"Cannot get 'items' property of node $coll"), _.items)
+    def items: Seq[Value[SType]] = matchCase(_.items, _ => sys.error(
+      s"""Unable to retrieve the 'items' property of node $coll.
+         |Please ensure the node is correctly initialized and has the items property available.
+         |For further assistance, refer to our node documentation.""".stripMargin.replaceAll("\n", " ")), _.items)
 
     /** Abstracts from details of pattern matching collection expressions.
       * Folds over given `coll` structure.
diff --git a/sc/shared/src/test/scala/sigma/SigmaDslTesting.scala b/sc/shared/src/test/scala/sigma/SigmaDslTesting.scala
index 31e873699b..45a8283472 100644
--- a/sc/shared/src/test/scala/sigma/SigmaDslTesting.scala
+++ b/sc/shared/src/test/scala/sigma/SigmaDslTesting.scala
@@ -843,7 +843,9 @@ class SigmaDslTesting extends AnyPropSpec
   )(implicit IR: IRContext, override val evalSettings: EvalSettings, val tA: RType[A], val tB: RType[B])
     extends Feature[A, B] {
     override def scalaFunc: A => B = { x =>
-      sys.error(s"Semantic Scala function is not defined for old implementation: $this")
+      sys.error(s"The Semantic Scala function is not defined for the current implementation: $this.
+      |Please update your implementation to the latest version.
+      |For more information, visit our Scala function documentation.".stripMargin.replaceAll("\n", " "))
     }
     implicit val cs = compilerSettingsInTests