First attempt at a light weight logging DSL that makes logging/debugging complicated processes easier to read.

fancy_logger_dsl.rb

require 'pry'
module Logger

  def log(title, opts = {})
    __blocks[title] = {
      successful: true,
      parent: __blocks[:current],
      cascade: opts.fetch(:cascade, false)
    }
    __blocks[:current] = title

    out("#{title} STARTED")

    inc_indent

    yield

    dec_indent

    out("#{title} #{(__blocks[title][:successful]) ? "COMPLETED" : "FAILED"}")
  end

  def out(text)
    puts indent + text
  end

  def error(text, exception)
    puts indent + "ERROR: #{text}"

    inc_indent
    puts indent + "Exception: #{exception}"
    dec_indent

    block = __blocks[__blocks[:current]]
    block[:successful] = false
    if block[:cascade]
      cascade_failure(block)
    end
  end

  protected

  def __blocks
    @__blocks ||= {}
  end

  private
  def indent
    (" " * @indent_level.to_i)
  end

  def inc_indent
    @indent_level = (@indent_level.to_i + 1)
  end

  def dec_indent
    @indent_level = (@indent_level.to_i - 1)
  end

  def cascade_failure(block)
    return if block.nil?
    block[:successful] = false
    cascade_failure(__blocks[block[:parent]])
  end
end

order_logger.rb

require_relative 'fancy_logger_dsl'
class OrderLogger
  include Logger

  def all
    log "all" do
      orders
    end
  end

  def orders
    # do non-log worthy thing here
    log "orders" do
      orders = []

      log "Writing to File: /tmp", cascade: true do
        begin
          #Write file
          raise "ERNOECS #{orders}" #some awful error
        rescue StandardError => e
          error "Couldn't save file", e
        end
      end
    end
  end
end

OrderLogger.new.all

output.txt

all STARTED
 orders STARTED
  Writing to File: /tmp STARTED
   ERROR: Couldn't save file
    Exception: ERNOECS []
  Writing to File: /tmp FAILED
 orders FAILED
all FAILED