Are you inside a loop? Here is a possible way of doing it

def check(td, tt, trigger, key, ticket_changes)
    if td.send(trigger)
      unless tt.changes.key?(key)
        @run = 0
        return true
      end
      unless tt.changes[key][1] == ticket_changes
        @run = 0
        return true
      end
    end
    return false
end

def metacheck(td, tt)
    [[:tt_closed, :status, "Closed"],
     [:tt_assignee, :assigned_to, td.tt_assignee]].each do |k|
        return if check(td, tt, k[0], k[1], k[2])
     end
end


metacheck(trigger_data, trouble_ticket)

I have used an array of triplets to check the conditions.

Are you inside a loop? Here is a possible way of doing it

def check(td, tt, trigger, key, ticket_changes)
    if td.send(trigger)
      unless tt.changes.key?(key)
        @run = 0
        return true
      end
      unless tt.changes[key][1] == ticket_changes
        @run = 0
        return true
      end
    end
    return false
end

def metacheck(td, tt)
    [[:tt_closed, :status, "Closed"],
     [:tt_assignee, :assigned_to, td.tt_assignee]].each do |k|
        return if check(td, tt, k[0], k[1], k[2])
     end
end


metacheck(trigger_data, trouble_ticket)

I have used an array of triplets to check the conditions. The check can further be simplified as

def check(td, tt, trigger, key, ticket_changes)
    return false unless td.send(trigger)
    if !tt.changes.key?(key) or (tt.changes[key][1] != ticket_changes)
        @run = 0
        return true
    end
    return false
end

We can join all the conditions together. But I think this captures the original intension best.