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Paperclip Error 422

I am having problems with paperclip. When I have a "#" after the size (for scaling and cropping), I get error 422. My log says this:

Command :: convert '/tmp/**** (20130110)20130311-13571-xxasmt.png[0]' -auto-orient -resize "150x150#" '/tmp/**** (20130110)20130311-13571-xxasmt20130311-13571-1anrx0y'
[paperclip] An error was received while processing: #<Paperclip::Error: There was an error processing the thumbnail for **** (20130110)20130311-13571-xxasmt>
Completed 422 Unprocessable Entity in 2785ms (Views: 0.8ms | ActiveRecord: 9.1ms)

This is my clip code in the model:

  has_attached_file :image,
  :styles => {
    :medium => "300x300#",
    :thumb => "100x100>",
    :standard => "150x150>"
  },
  :storage => :s3,
  :s3_credentials => "#{Rails.root}/config/s3.yml",
  :bucket => "convertkit",
  :s3_protocol => "https"

Did I miss something?

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has_attached_file :avatar,
                :styles => {
                          :thumb => "60x60>", :medium => "120x120>",
                          :original => "100%", small2: "65x65>", medium2: "144x144>"
                          },
                          :storage => :s3,
                          :s3_credentials => "#{::Rails.root.to_s}/config/aws.yml",
                          :s3_permissions => "public-read",
                          :url => ':s3_alias_url',
                          :path => "/slider/:attachment/:id_partition/:style/:filename",
                          :s3_host_alias => Settings.cloud_front_url,
                          :s3_protocol => :https,
                          :s3_headers => {'Expires' => (Time.now + 6060243012).httpdate},
                          default_url: "paperclip_default/slider/:style_missing.png"
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