diff --git a/src/array.cr b/src/array.cr
index cef70c4704c7..30425c6869e3 100644
--- a/src/array.cr
+++ b/src/array.cr
@@ -1658,7 +1658,7 @@ class Array(T)
   # Raises `ArgumentError` if for any two elements the block returns `nil`.
   def sort(&block : T, T -> U) : Array(T) forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#sort_by`?" %}
     {% end %}
 
     dup.sort! &block
@@ -1680,7 +1680,7 @@ class Array(T)
   # Raises `ArgumentError` if for any two elements the block returns `nil`.
   def unstable_sort(&block : T, T -> U) : Array(T) forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#unstable_sort_by`?" %}
     {% end %}
 
     dup.unstable_sort!(&block)
@@ -1701,7 +1701,7 @@ class Array(T)
   # :inherit:
   def sort!(&block : T, T -> U) : self forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#sort_by!`?" %}
     {% end %}
 
     to_unsafe_slice.sort!(&block)
@@ -1711,7 +1711,7 @@ class Array(T)
   # :inherit:
   def unstable_sort!(&block : T, T -> U) : self forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#unstable_sort_by!`?" %}
     {% end %}
 
     to_unsafe_slice.unstable_sort!(&block)
diff --git a/src/slice.cr b/src/slice.cr
index 7a27218221a2..196a29a768dd 100644
--- a/src/slice.cr
+++ b/src/slice.cr
@@ -932,7 +932,7 @@ struct Slice(T)
   # Raises `ArgumentError` if for any two elements the block returns `nil`.
   def sort(&block : T, T -> U) : self forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#sort_by`?" %}
     {% end %}
 
     dup.sort! &block
@@ -954,7 +954,7 @@ struct Slice(T)
   # Raises `ArgumentError` if for any two elements the block returns `nil`.
   def unstable_sort(&block : T, T -> U) : self forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#unstable_sort_by`?" %}
     {% end %}
 
     dup.unstable_sort!(&block)
@@ -1055,7 +1055,7 @@ struct Slice(T)
   # Raises `ArgumentError` if for any two elements the block returns `nil`.
   def sort!(&block : T, T -> U) : self forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#sort_by!`?" %}
     {% end %}
 
     Slice.merge_sort!(self, block)
@@ -1098,7 +1098,7 @@ struct Slice(T)
   # Raises `ArgumentError` if for any two elements the block returns `nil`.
   def unstable_sort!(&block : T, T -> U) : self forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#unstable_sort_by!`?" %}
     {% end %}
 
     Slice.intro_sort!(to_unsafe, size, block)
diff --git a/src/static_array.cr b/src/static_array.cr
index 4cb2b186f200..2c09e21df166 100644
--- a/src/static_array.cr
+++ b/src/static_array.cr
@@ -228,7 +228,7 @@ struct StaticArray(T, N)
   # Raises `ArgumentError` if for any two elements the block returns `nil`.=
   def sort(&block : T, T -> U) : StaticArray(T, N) forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#sort_by`?" %}
     {% end %}
 
     ary = dup
@@ -251,7 +251,7 @@ struct StaticArray(T, N)
   # Raises `ArgumentError` if for any two elements the block returns `nil`.
   def unstable_sort(&block : T, T -> U) : StaticArray(T, N) forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#unstable_sort_by`?" %}
     {% end %}
 
     ary = dup
@@ -273,7 +273,7 @@ struct StaticArray(T, N)
   # :inherit:
   def sort!(&block : T, T -> U) : self forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#sort_by!`?" %}
     {% end %}
 
     to_slice.sort!(&block)
@@ -283,7 +283,7 @@ struct StaticArray(T, N)
   # :inherit:
   def unstable_sort!(&block : T, T -> U) : self forall U
     {% unless U <= Int32? %}
-      {% raise "Expected block to return Int32 or Nil, not #{U}" %}
+      {% raise "Expected block to return Int32 or Nil, not #{U}.\nThe block is supposed to be a custom comparison operation, compatible with `Comparable#<=>`.\nDid you mean to use `#unstable_sort_by!`?" %}
     {% end %}
 
     to_slice.unstable_sort!(&block)