Callback message printing not working as intended with retry logic

I am trying to make a program that does the following:

1. Processes a list of items.
2. Each item is processed by a dedicated function.
3. Each function call is wrapped in a with_retries block function.
4. Display messages are supposed to be displayed using callbacks.

I have successfully implemented callbacks, error handling, and retry logic, but there is something wrong in my implementation, because combining callbacks with retry logic breaks error handling.

This program:

def print_attempt_number(proc_id:, &callback)    random = [true, false].sample    if random        message = "Attempt for ID: #{proc_id}"        callback.call(proc_id, message) if callback        # puts "PUTS: #{message}"    else        raise StandardError, "This is my error message"    endenddef handle_error(proc_id:, retries:, max_retries:, &callback)    retries += 1    retry_msg = "Retry #{retries} / #{max_retries}"    # puts "PUTS: #{retry_msg}"    callback.call(proc_id, retry_msg)    return retriesenddef with_retries(max_retries:, proc_id:, &callback)    retries = 0    begin        yield    rescue StandardError => e        retries = handle_error(proc_id: proc_id, retries: retries, max_retries: max_retries, &callback)        sleep 1.0        retry if retries < max_retries    endenddef process_item(proc_id:, &callback)    init_msg = "Starting with #{proc_id}"    callback.call(proc_id, init_msg)    with_retries(max_retries: 3, proc_id:) do        print_attempt_number(proc_id: proc_id, &callback)    endendcallback = Proc.new do |proc_id, message|    puts "CALLBACK: #{proc_id}\t#{message}"endfor id in 1..5 do    process_item(proc_id: id, &callback)    sleep 1.0end

Produces this result:

CALLBACK: 1     Starting with 1CALLBACK: 1     Attempt for ID: 1CALLBACK: 2     Starting with 2CALLBACK: 2     Attempt for ID: 2callback_test.rb:8:in `print_attempt_number': This is my error message (StandardError)        from callback_test.rb:38:in `block in process_item'        from callback_test.rb:16:in `handle_error'        from callback_test.rb:25:in `rescue in with_retries'        from callback_test.rb:22:in `with_retries'        from callback_test.rb:37:in `process_item'        from callback_test.rb:49:in `block in <main>'        from callback_test.rb:48:in `each'        from callback_test.rb:48:in `<main>'callback_test.rb:8:in `print_attempt_number': This is my error message (StandardError)        from callback_test.rb:38:in `block in process_item'        from callback_test.rb:23:in `with_retries'        from callback_test.rb:37:in `process_item'        from callback_test.rb:49:in `block in <main>'        from callback_test.rb:48:in `each'        from callback_test.rb:48:in `<main>'

However, switching from callback directly to puts produces the results as expected:

def print_attempt_number(proc_id:, &callback)    random = [true, false].sample    if random        message = "Attempt for ID: #{proc_id}"        # callback.call(proc_id, message) if callback        puts "PUTS: #{message}"    else        raise StandardError, "This is my error message"    endenddef handle_error(proc_id:, retries:, max_retries:, &callback)    retries += 1    retry_msg = "Retry #{retries} / #{max_retries}"    puts "PUTS: #{retry_msg}"    # callback.call(proc_id, retry_msg)    return retriesenddef with_retries(max_retries:, proc_id:, &callback)    retries = 0    begin        yield    rescue StandardError => e        retries = handle_error(proc_id: proc_id, retries: retries, max_retries: max_retries, &callback)        sleep 1.0        retry if retries < max_retries    endenddef process_item(proc_id:, &callback)    init_msg = "Starting with #{proc_id}"    callback.call(proc_id, init_msg)    with_retries(max_retries: 3, proc_id:) do        print_attempt_number(proc_id: proc_id, &callback)    endendcallback = Proc.new do |proc_id, message|    puts "CALLBACK: #{proc_id}\t#{message}"endfor id in 1..5 do    process_item(proc_id: id, &callback)    sleep 1.0end

Which produces:

CALLBACK: 1     Starting with 1PUTS: Attempt for ID: 1CALLBACK: 2     Starting with 2PUTS: Retry 1 / 3PUTS: Attempt for ID: 2CALLBACK: 3     Starting with 3PUTS: Retry 1 / 3PUTS: Attempt for ID: 3CALLBACK: 4     Starting with 4PUTS: Retry 1 / 3PUTS: Retry 2 / 3PUTS: Retry 3 / 3CALLBACK: 5     Starting with 5PUTS: Attempt for ID: 5

I don't understand why that happens; how can I achieve the desired printing using callback for print messages?