diff --git a/features/basics/pretty-print.feature b/features/basics/pretty-print.feature
new file mode 100644
index 0000000..af88f49
--- /dev/null
+++ b/features/basics/pretty-print.feature
@@ -0,0 +1,241 @@
+Feature: Pretty printing Contract violations
+
+  Scenario: Big array argument being passed to big array method parameter
+    Given a file named "example.rb" with:
+    """ruby
+    require "contracts"
+    C = Contracts
+
+    class Example
+      include Contracts::Core
+
+      class << self
+        Contract [
+            C::Or[String, Symbol],
+            C::Or[String, Symbol],
+            C::Or[String, Symbol],
+            C::Or[String, Symbol],
+            C::Or[String, Symbol],
+            C::Or[String, Symbol],
+            C::Or[String, Symbol]
+        ] => nil
+        def run(data)
+          nil
+        end
+      end
+    end
+
+    puts Example.run([
+      ["foo", "foo"],
+      ["foo", "foo"],
+      ["foo", "foo"],
+      ["foo", "foo"],
+      ["foo", "foo"],
+      ["foo", "foo"],
+      ["foo", "foo"],
+      ["foo", "foo"],
+      ["foo", "foo"]
+    ])
+    """
+    When I run `ruby example.rb`
+    Then the output should contain:
+    """
+    : Contract violation for argument 1 of 1: (ParamContractError)
+            Expected: [(String or Symbol),
+                       (String or Symbol),
+                       (String or Symbol),
+                       (String or Symbol),
+                       (String or Symbol),
+                       (String or Symbol),
+                       (String or Symbol)],
+            Actual: [["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"]]
+            Value guarded in: Example::run
+            With Contract: Array => NilClass
+            At: example.rb:17
+    """
+
+  Scenario: Big array value being returned from method expecting different big array type
+    Given a file named "example.rb" with:
+    """ruby
+    require "contracts"
+    C = Contracts
+
+    class Example
+      include Contracts::Core
+
+      class << self
+        Contract C::None => [
+            C::Or[String, Symbol],
+            C::Or[String, Symbol],
+            C::Or[String, Symbol],
+            C::Or[String, Symbol],
+            C::Or[String, Symbol],
+            C::Or[String, Symbol],
+            C::Or[String, Symbol]
+        ]
+        def run
+          [
+            ["foo", "foo"],
+            ["foo", "foo"],
+            ["foo", "foo"],
+            ["foo", "foo"],
+            ["foo", "foo"],
+            ["foo", "foo"],
+            ["foo", "foo"],
+            ["foo", "foo"],
+            ["foo", "foo"]
+          ]
+        end
+      end
+    end
+
+    puts Example.run
+    """
+    When I run `ruby example.rb`
+    Then the output should contain:
+    """
+    : Contract violation for return value: (ReturnContractError)
+            Expected: [(String or Symbol),
+                       (String or Symbol),
+                       (String or Symbol),
+                       (String or Symbol),
+                       (String or Symbol),
+                       (String or Symbol),
+                       (String or Symbol)],
+            Actual: [["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"],
+                     ["foo", "foo"]]
+            Value guarded in: Example::run
+            With Contract: None => Array
+            At: example.rb:17
+    """
+
+  Scenario: Big hash argument being passed to big hash method parameter
+    Given a file named "example.rb" with:
+    """ruby
+    require "contracts"
+    C = Contracts
+
+    class Example
+      include Contracts::Core
+
+      class << self
+        Contract ({
+            a: C::Or[String, Symbol],
+            b: C::Or[String, Symbol],
+            c: C::Or[String, Symbol],
+            d: C::Or[String, Symbol],
+            e: C::Or[String, Symbol],
+            f: C::Or[String, Symbol],
+            g: C::Or[String, Symbol]
+        }) => nil
+        def run(data)
+          nil
+        end
+      end
+    end
+
+    puts Example.run({
+      a: ["foo", "foo"],
+      b: ["foo", "foo"],
+      c: ["foo", "foo"],
+      d: ["foo", "foo"],
+      e: ["foo", "foo"],
+      f: ["foo", "foo"],
+      g: ["foo", "foo"]
+    })
+    """
+    When I run `ruby example.rb`
+    Then the output should contain:
+    """
+    : Contract violation for argument 1 of 1: (ParamContractError)
+            Expected: {:a=>(String or Symbol),
+                       :b=>(String or Symbol),
+                       :c=>(String or Symbol),
+                       :d=>(String or Symbol),
+                       :e=>(String or Symbol),
+                       :f=>(String or Symbol),
+                       :g=>(String or Symbol)},
+            Actual: {:a=>["foo", "foo"],
+                     :b=>["foo", "foo"],
+                     :c=>["foo", "foo"],
+                     :d=>["foo", "foo"],
+                     :e=>["foo", "foo"],
+                     :f=>["foo", "foo"],
+                     :g=>["foo", "foo"]}
+            Value guarded in: Example::run
+            With Contract: Hash => NilClass
+            At: example.rb:17
+    """
+
+  Scenario: Big hash value being returned from method expecting different big hash type
+    Given a file named "example.rb" with:
+    """ruby
+    require "contracts"
+    C = Contracts
+
+    class Example
+      include Contracts::Core
+
+      class << self
+        Contract C::None => ({
+            a: C::Or[String, Symbol],
+            b: C::Or[String, Symbol],
+            c: C::Or[String, Symbol],
+            d: C::Or[String, Symbol],
+            e: C::Or[String, Symbol],
+            f: C::Or[String, Symbol],
+            g: C::Or[String, Symbol]
+        })
+        def run
+          {
+            a: ["foo", "foo"],
+            b: ["foo", "foo"],
+            c: ["foo", "foo"],
+            d: ["foo", "foo"],
+            e: ["foo", "foo"],
+            f: ["foo", "foo"],
+            g: ["foo", "foo"]
+          }
+        end
+      end
+    end
+
+    puts Example.run
+    """
+    When I run `ruby example.rb`
+    Then the output should contain:
+    """
+    : Contract violation for return value: (ReturnContractError)
+            Expected: {:a=>(String or Symbol),
+                       :b=>(String or Symbol),
+                       :c=>(String or Symbol),
+                       :d=>(String or Symbol),
+                       :e=>(String or Symbol),
+                       :f=>(String or Symbol),
+                       :g=>(String or Symbol)},
+            Actual: {:a=>["foo", "foo"],
+                     :b=>["foo", "foo"],
+                     :c=>["foo", "foo"],
+                     :d=>["foo", "foo"],
+                     :e=>["foo", "foo"],
+                     :f=>["foo", "foo"],
+                     :g=>["foo", "foo"]}
+            Value guarded in: Example::run
+            With Contract: None => Hash
+            At: example.rb:17
+    """
diff --git a/lib/contracts.rb b/lib/contracts.rb
index baf2acf..a4303d0 100644
--- a/lib/contracts.rb
+++ b/lib/contracts.rb
@@ -116,22 +116,57 @@ def to_s
   # This function is used by the default #failure_callback method
   # and uses the hash passed into the failure_callback method.
   def self.failure_msg(data)
-    expected = Contracts::Formatters::Expected.new(data[:contract]).contract
-    position = Contracts::Support.method_position(data[:method])
+    indent_amount = 8
     method_name = Contracts::Support.method_name(data[:method])
 
+    # Header
     header = if data[:return_value]
                "Contract violation for return value:"
              else
                "Contract violation for argument #{data[:arg_pos]} of #{data[:total_args]}:"
              end
 
-    %{#{header}
-        Expected: #{expected},
-        Actual: #{data[:arg].inspect}
-        Value guarded in: #{data[:class]}::#{method_name}
-        With Contract: #{data[:contracts]}
-        At: #{position} }
+    # Expected
+    expected_prefix = "Expected: "
+    expected_value = Contracts::Support.indent_string(
+      Contracts::Formatters::Expected.new(data[:contract]).contract.pretty_inspect,
+      expected_prefix.length
+    ).strip
+    expected_line = expected_prefix + expected_value + ","
+
+    # Actual
+    actual_prefix = "Actual: "
+    actual_value = Contracts::Support.indent_string(
+      data[:arg].pretty_inspect,
+      actual_prefix.length
+    ).strip
+    actual_line = actual_prefix + actual_value
+
+    # Value guarded in
+    value_prefix = "Value guarded in: "
+    value_value = "#{data[:class]}::#{method_name}"
+    value_line = value_prefix + value_value
+
+    # Contract
+    contract_prefix = "With Contract: "
+    contract_value = data[:contracts].to_s
+    contract_line = contract_prefix + contract_value
+
+    # Position
+    position_prefix = "At: "
+    position_value = Contracts::Support.method_position(data[:method])
+    position_line = position_prefix + position_value
+
+    header +
+      "\n" +
+      Contracts::Support.indent_string(
+        [expected_line,
+         actual_line,
+         value_line,
+         contract_line,
+         position_line].join("\n"),
+        indent_amount
+      )
   end
 
   # Callback for when a contract fails. By default it raises
diff --git a/lib/contracts/formatters.rb b/lib/contracts/formatters.rb
index db9b107..2d4f70b 100644
--- a/lib/contracts/formatters.rb
+++ b/lib/contracts/formatters.rb
@@ -1,3 +1,5 @@
+require "pp"
+
 module Contracts
   # A namespace for classes related to formatting.
   module Formatters
@@ -25,13 +27,13 @@ def hash_contract(hash)
         @full = true # Complex values output completely, overriding @full
         hash.inject({}) do |repr, (k, v)|
           repr.merge(k => InspectWrapper.create(contract(v), @full))
-        end.inspect
+        end
       end
 
       # Formats Array contracts.
       def array_contract(array)
         @full = true
-        array.map { |v| InspectWrapper.create(contract(v), @full) }.inspect
+        array.map { |v| InspectWrapper.create(contract(v), @full) }
       end
     end
 
diff --git a/lib/contracts/support.rb b/lib/contracts/support.rb
index f3efa20..cda3a55 100644
--- a/lib/contracts/support.rb
+++ b/lib/contracts/support.rb
@@ -42,6 +42,13 @@ def eigenclass?(target)
           target <= eigenclass_of(Object)
       end
 
+      def indent_string(string, amount)
+        string.gsub(
+          /^(?!$)/,
+          (string[/^[ \t]/] || " ") * amount
+        )
+      end
+
       private
 
       # Module eigenclass can be detected by its ancestor chain
diff --git a/spec/contracts_spec.rb b/spec/contracts_spec.rb
index d37c40e..56be470 100644
--- a/spec/contracts_spec.rb
+++ b/spec/contracts_spec.rb
@@ -637,6 +637,28 @@ def delim(match)
       end.to raise_error(ContractError, not_s(delim "String or Symbol"))
     end
 
+    it "should wrap and pretty print for long param contracts" do
+      expect do
+        @o.long_array_param_contracts(true)
+      end.to(
+        raise_error(
+          ParamContractError,
+          /\[\(String or Symbol\),\n                   \(String or Symbol\),/
+        )
+      )
+    end
+
+    it "should wrap and pretty print for long return contracts" do
+      expect do
+        @o.long_array_return_contracts
+      end.to(
+        raise_error(
+          ReturnContractError,
+          /\[\(String or Symbol\),\n                   \(String or Symbol\),/
+        )
+      )
+    end
+
     it "should not contain Contracts:: module prefix" do
       expect do
         @o.double("bad")
diff --git a/spec/fixtures/fixtures.rb b/spec/fixtures/fixtures.rb
index b6d2bea..67b5740 100644
--- a/spec/fixtures/fixtures.rb
+++ b/spec/fixtures/fixtures.rb
@@ -152,6 +152,30 @@ def array_complex_contracts(data)
   def nested_array_complex_contracts(data)
   end
 
+  Contract [
+    C::Or[String, Symbol],
+    C::Or[String, Symbol],
+    C::Or[String, Symbol],
+    C::Or[String, Symbol],
+    C::Or[String, Symbol],
+    C::Or[String, Symbol],
+    C::Or[String, Symbol]
+  ] => nil
+  def long_array_param_contracts(data)
+  end
+
+  Contract C::None => [
+    C::Or[String, Symbol],
+    C::Or[String, Symbol],
+    C::Or[String, Symbol],
+    C::Or[String, Symbol],
+    C::Or[String, Symbol],
+    C::Or[String, Symbol],
+    C::Or[String, Symbol]
+  ]
+  def long_array_return_contracts
+  end
+
   Contract Proc => C::Any
   def do_call(&block)
     block.call