diff --git a/app/jobs/generate_party_preview_job.rb b/app/jobs/generate_party_preview_job.rb
index b73a7f4..4453c83 100644
--- a/app/jobs/generate_party_preview_job.rb
+++ b/app/jobs/generate_party_preview_job.rb
@@ -13,7 +13,10 @@ class GeneratePartyPreviewJob < ApplicationJob
 
   def perform(party_id)
     Rails.logger.info("Starting preview generation for party #{party_id}")
+    Rails.logger.info("Debug: should_generate? check starting")
+
     party = Party.find(party_id)
+    Rails.logger.info("Party found: #{party.inspect}")
 
     if party.preview_state == 'generated' &&
       party.preview_generated_at &&
@@ -23,9 +26,22 @@ class GeneratePartyPreviewJob < ApplicationJob
     end
 
     begin
+      Rails.logger.info("Initializing PreviewService::Coordinator")
       service = PreviewService::Coordinator.new(party)
-      Rails.logger.info("Created PreviewService::Coordinator")
+      Rails.logger.info("Coordinator initialized")
 
+      Rails.logger.info("Checking should_generate?")
+      should_gen = service.send(:should_generate?)
+      Rails.logger.info("should_generate? returned: #{should_gen}")
+
+      if !should_gen
+        Rails.logger.info("Not generating preview because should_generate? returned false")
+        Rails.logger.info("Preview state: #{party.preview_state}")
+        Rails.logger.info("Generation in progress: #{service.send(:generation_in_progress?)}")
+        return
+      end
+
+      Rails.logger.info("Starting generate_preview")
       result = service.generate_preview
       Rails.logger.info("Generate preview result: #{result}")
 
@@ -38,7 +54,7 @@ class GeneratePartyPreviewJob < ApplicationJob
     rescue => e
       Rails.logger.error("Error generating preview for party #{party_id}: #{e.message}")
       Rails.logger.error("Full error details:")
-      Rails.logger.error(e.full_message) # This will include the stack trace
+      Rails.logger.error(e.full_message)
       notify_failure(party, e)
       raise
     end
diff --git a/app/models/party.rb b/app/models/party.rb
index f0944e7..f1bebc2 100644
--- a/app/models/party.rb
+++ b/app/models/party.rb
@@ -106,10 +106,11 @@ class Party < ApplicationRecord
   attr_accessor :favorited
 
   self.enum :preview_state, {
-    pending: 0, # Never generated
-    queued: 1, # Generation job scheduled
-    generated: 2, # Has preview image
-    failed: 3 # Generation failed
+    pending: 0,
+    queued: 1,
+    in_progress: 2,
+    generated: 3,
+    failed: 4
   }
 
   after_commit :schedule_preview_regeneration, if: :preview_relevant_changes?
diff --git a/app/services/preview_service/canvas.rb b/app/services/preview_service/canvas.rb
index 1477ec0..a632635 100644
--- a/app/services/preview_service/canvas.rb
+++ b/app/services/preview_service/canvas.rb
@@ -15,26 +15,31 @@ module PreviewService
     end
 
     def create_blank_canvas(width: PREVIEW_WIDTH, height: PREVIEW_HEIGHT, color: DEFAULT_BACKGROUND_COLOR)
-      Rails.logger.info("Checking ImageMagick installation...")
-      version = `convert -version`
-      Rails.logger.info("ImageMagick version: #{version}")
-
+      Rails.logger.info("Creating blank canvas #{width}x#{height}")
       temp_file = Tempfile.new(%w[canvas .png])
-      Rails.logger.info("Created temp file: #{temp_file.path}")
+      Rails.logger.info("Temp file created at: #{temp_file.path}")
 
       begin
+        Rails.logger.info("Checking ImageMagick setup...")
+        version = `which convert`
+        Rails.logger.info("ImageMagick convert path: #{version}")
+
+        Rails.logger.info("Executing convert command...")
         MiniMagick::Tool::Convert.new do |convert|
           convert.size "#{width}x#{height}"
           convert << "xc:#{color}"
           convert << temp_file.path
         end
-        Rails.logger.info("Canvas created successfully")
+        Rails.logger.info("Convert command completed successfully")
       rescue => e
-        Rails.logger.error("Failed to create canvas: #{e.message}")
+        Rails.logger.error("Failed to create canvas with convert: #{e.class} - #{e.message}")
+        Rails.logger.error("PATH: #{ENV['PATH']}")
+        Rails.logger.error("LD_LIBRARY_PATH: #{ENV['LD_LIBRARY_PATH']}")
         Rails.logger.error(e.backtrace.join("\n"))
         raise
       end
 
+      Rails.logger.info("Canvas created successfully at: #{temp_file.path}")
       temp_file
     end
 
@@ -43,7 +48,12 @@ module PreviewService
       font_color = options.fetch(:color, 'white')
 
       # Load custom font for username, for later use
-      @font_path ||= Rails.root.join('app', 'assets', 'fonts', 'Gk-Bd.otf').to_s
+      @font_path = Rails.root.join('app', 'assets', 'fonts', 'Gk-Bd.otf').to_s
+      Rails.logger.info("Using font path: #{@font_path}")
+      unless File.exist?(@font_path)
+        Rails.logger.error("Font file not found at: #{@font_path}")
+        raise "Font file not found"
+      end
 
       # Measure party name text size
       text_metrics = measure_text(party_name, font_size)
diff --git a/app/services/preview_service/coordinator.rb b/app/services/preview_service/coordinator.rb
index 2fad8a6..90409f7 100644
--- a/app/services/preview_service/coordinator.rb
+++ b/app/services/preview_service/coordinator.rb
@@ -39,15 +39,38 @@ module PreviewService
 
       begin
         Rails.logger.info("Starting preview generation for party #{@party.id}")
+
+        # Update state to in_progress
+        @party.update!(preview_state: :in_progress)
         set_generation_in_progress
 
+        Rails.logger.info("Checking ImageMagick installation...")
+        begin
+          version = `convert -version`
+          Rails.logger.info("ImageMagick version: #{version}")
+        rescue => e
+          Rails.logger.error("Failed to get ImageMagick version: #{e.message}")
+        end
+
         Rails.logger.info("Creating preview image...")
-        image = create_preview_image
-        Rails.logger.info("Preview image created successfully")
+        begin
+          image = create_preview_image
+          Rails.logger.info("Preview image created successfully")
+        rescue => e
+          Rails.logger.error("Failed to create preview image: #{e.class} - #{e.message}")
+          Rails.logger.error(e.backtrace.join("\n"))
+          raise e
+        end
 
         Rails.logger.info("Saving preview...")
-        save_preview(image)
-        Rails.logger.info("Preview saved successfully")
+        begin
+          save_preview(image)
+          Rails.logger.info("Preview saved successfully")
+        rescue => e
+          Rails.logger.error("Failed to save preview: #{e.class} - #{e.message}")
+          Rails.logger.error(e.backtrace.join("\n"))
+          raise e
+        end
 
         Rails.logger.info("Updating party state...")
         @party.update!(
@@ -58,7 +81,7 @@ module PreviewService
 
         true
       rescue => e
-        Rails.logger.error("Failed to generate preview: #{e.class} - #{e.message}")
+        Rails.logger.error("Preview generation failed: #{e.class} - #{e.message}")
         Rails.logger.error("Stack trace:")
         Rails.logger.error(e.backtrace.join("\n"))
         handle_preview_generation_error(e)
@@ -95,6 +118,38 @@ module PreviewService
       Rails.logger.error("Failed to delete preview for party #{@party.id}: #{e.message}")
     end
 
+    # Determines if a new preview should be generated
+    #
+    # @return [Boolean] True if a new preview should be generated, false otherwise
+    def should_generate?
+      Rails.logger.info("Checking should_generate? conditions")
+
+      if generation_in_progress?
+        Rails.logger.info("Generation already in progress, returning false")
+        return false
+      end
+
+      Rails.logger.info("Preview state: #{@party.preview_state}")
+      # Add 'queued' to the list of valid states for generation
+      if @party.preview_state.in?(['pending', 'failed', 'queued'])
+        Rails.logger.info("Preview state is #{@party.preview_state}, returning true")
+        return true
+      end
+
+      if @party.preview_state == 'generated'
+        if @party.preview_generated_at < PREVIEW_EXPIRY.ago
+          Rails.logger.info("Preview is older than expiry time, returning true")
+          return true
+        else
+          Rails.logger.info("Preview is recent, returning false")
+          return false
+        end
+      end
+
+      Rails.logger.info("No conditions met, returning false")
+      false
+    end
+
     private
 
     # Sets up the appropriate storage system based on environment
@@ -111,33 +166,61 @@ module PreviewService
     # @return [MiniMagick::Image] The generated preview image
     def create_preview_image
       Rails.logger.info("Creating blank canvas...")
-      canvas = @canvas_service.create_blank_canvas
-      image = MiniMagick::Image.new(canvas.path)
-      Rails.logger.info("Blank canvas created")
+      begin
+        canvas = @canvas_service.create_blank_canvas
+        Rails.logger.info("Canvas created at: #{canvas.path}")
+        image = MiniMagick::Image.new(canvas.path)
+        Rails.logger.info("MiniMagick image object created")
+      rescue => e
+        Rails.logger.error("Failed to create canvas: #{e.class} - #{e.message}")
+        Rails.logger.error(e.backtrace.join("\n"))
+        raise e
+      end
 
+      # Add more detailed logging for job icon handling
       Rails.logger.info("Processing job icon...")
       job_icon = nil
       if @party.job.present?
+        Rails.logger.info("Job present: #{@party.job.inspect}")
         Rails.logger.info("Fetching job icon for job ID: #{@party.job.granblue_id}")
-        job_icon = @image_fetcher.fetch_job_icon(@party.job.granblue_id)
-        Rails.logger.info("Job icon fetched successfully") if job_icon
+        begin
+          job_icon = @image_fetcher.fetch_job_icon(@party.job.granblue_id)
+          Rails.logger.info("Job icon fetched successfully") if job_icon
+        rescue => e
+          Rails.logger.error("Failed to fetch job icon: #{e.class} - #{e.message}")
+          Rails.logger.error(e.backtrace.join("\n"))
+          # Don't raise this error, just log it and continue without the job icon
+        end
       end
 
-      Rails.logger.info("Adding party name and job icon...")
-      text_result = @canvas_service.add_text(image, @party.name, job_icon: job_icon, user: @party.user)
-      image = text_result[:image]
-      Rails.logger.info("Party name and job icon added")
+      begin
+        Rails.logger.info("Adding party name and job icon...")
+        text_result = @canvas_service.add_text(image, @party.name, job_icon: job_icon, user: @party.user)
+        image = text_result[:image]
+        Rails.logger.info("Text and icon added successfully")
+      rescue => e
+        Rails.logger.error("Failed to add text/icon: #{e.class} - #{e.message}")
+        Rails.logger.error(e.backtrace.join("\n"))
+        raise e
+      end
 
-      Rails.logger.info("Calculating grid layout...")
-      grid_layout = @grid_service.calculate_layout(
-        canvas_height: Canvas::PREVIEW_HEIGHT,
-        title_bottom_y: text_result[:text_bottom_y]
-      )
-      Rails.logger.info("Grid layout calculated")
+      begin
+        Rails.logger.info("Calculating grid layout...")
+        grid_layout = @grid_service.calculate_layout(
+          canvas_height: Canvas::PREVIEW_HEIGHT,
+          title_bottom_y: text_result[:text_bottom_y]
+        )
+        Rails.logger.info("Grid layout calculated")
 
-      Rails.logger.info("Drawing weapons...")
-      image = organize_and_draw_weapons(image, grid_layout)
-      Rails.logger.info("Weapons drawn successfully")
+        Rails.logger.info("Drawing weapons...")
+        Rails.logger.info("Weapons count: #{@party.weapons.count}")
+        image = organize_and_draw_weapons(image, grid_layout)
+        Rails.logger.info("Weapons drawn successfully")
+      rescue => e
+        Rails.logger.error("Failed during weapons drawing: #{e.class} - #{e.message}")
+        Rails.logger.error(e.backtrace.join("\n"))
+        raise e
+      end
 
       image
     end
@@ -310,25 +393,13 @@ module PreviewService
       )
     end
 
-    # Determines if a new preview should be generated
-    #
-    # @return [Boolean] True if a new preview should be generated, false otherwise
-    def should_generate?
-      return false if generation_in_progress?
-      return true if @party.preview_state.in?(['pending', 'failed'])
-
-      if @party.preview_state == 'generated'
-        return @party.preview_generated_at < PREVIEW_EXPIRY.ago
-      end
-
-      false
-    end
-
     # Checks if a preview generation is currently in progress
     #
     # @return [Boolean] True if a preview is being generated, false otherwise
     def generation_in_progress?
-      Rails.cache.exist?("party_preview_generating_#{@party.id}")
+      in_progress = Rails.cache.exist?("party_preview_generating_#{@party.id}")
+      Rails.logger.info("Cache key check for generation_in_progress: #{in_progress}")
+      in_progress
     end
 
     # Marks the preview generation as in progress
diff --git a/db/migrate/20250119062554_add_preview_s3_key_to_parties.rb b/db/migrate/20250119062554_add_preview_s3_key_to_parties.rb
new file mode 100644
index 0000000..b698ef4
--- /dev/null
+++ b/db/migrate/20250119062554_add_preview_s3_key_to_parties.rb
@@ -0,0 +1,5 @@
+class AddPreviewS3KeyToParties < ActiveRecord::Migration[8.0]
+  def change
+    add_column :parties, :preview_s3_key, :string
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index ffaeb01..b07f427 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[8.0].define(version: 2025_01_18_135254) do
+ActiveRecord::Schema[8.0].define(version: 2025_01_19_062554) do
   # These are extensions that must be enabled in order to support this database
   enable_extension "btree_gin"
   enable_extension "pg_catalog.plpgsql"
@@ -302,6 +302,7 @@ ActiveRecord::Schema[8.0].define(version: 2025_01_18_135254) do
     t.integer "visibility", default: 1, null: false
     t.integer "preview_state", default: 0, null: false
     t.datetime "preview_generated_at"
+    t.string "preview_s3_key"
     t.index ["accessory_id"], name: "index_parties_on_accessory_id"
     t.index ["guidebook1_id"], name: "index_parties_on_guidebook1_id"
     t.index ["guidebook2_id"], name: "index_parties_on_guidebook2_id"
diff --git a/lib/post_deployment/manager.rb b/lib/post_deployment/manager.rb
index 64a24f8..a997a9e 100644
--- a/lib/post_deployment/manager.rb
+++ b/lib/post_deployment/manager.rb
@@ -85,7 +85,8 @@ module PostDeployment
     def rebuild_search_indices
       SearchIndexer.new(
         test_mode: @test_mode,
-        verbose: @verbose
+        verbose: @verbose,
+        new_records: @new_records
       ).rebuild_all
     end
 
diff --git a/lib/post_deployment/search_indexer.rb b/lib/post_deployment/search_indexer.rb
index 8fee55d..786bf46 100644
--- a/lib/post_deployment/search_indexer.rb
+++ b/lib/post_deployment/search_indexer.rb
@@ -6,9 +6,10 @@ module PostDeployment
   class SearchIndexer
     include LoggingHelper
 
-    def initialize(test_mode:, verbose:)
+    def initialize(test_mode:, verbose:, new_records: {})
       @test_mode = test_mode
       @verbose = verbose
+      @new_records = new_records
     end
 
     def rebuild_all
@@ -38,12 +39,22 @@ module PostDeployment
     end
 
     def rebuild_index_for(model)
+      # Determine model type (lowercase, pluralized)
+      model_type = model.name.downcase.pluralize
+
+      # Check if there are new records for this model type
+      new_records = @new_records[model_type] || []
+
       if @test_mode
-        log_step "Would rebuild search index for #{model.name}"
+        log_step "Would rebuild search index for #{model.name}" if new_records.any?
       else
-        log_verbose "• #{model.name}... "
-        PgSearch::Multisearch.rebuild(model)
-        log_verbose "✅ done!\n"
+        if new_records.any?
+          log_verbose "• #{model.name}... "
+          PgSearch::Multisearch.rebuild(model)
+          log_verbose "✅ done! (#{new_records.size} new records)\n"
+        else
+          log_step "Skipping #{model.name} - no new records" if @verbose
+        end
       end
     rescue StandardError => e
       log_error("Failed to rebuild index for #{model.name}: #{e.message}")
diff --git a/railway.toml b/railway.toml
index 2cdf95e..ee5c10a 100644
--- a/railway.toml
+++ b/railway.toml
@@ -1,9 +1,20 @@
 [phases.setup]
 nixPkgs = [
     "imagemagick",
-    "ghostscript", # For PDF/PS operations
-    "pkgconfig", # For gem compilation
-    "libmagickwand" # ImageMagick C library
+    # For PDF/PS operations
+    "ghostscript",
+    # For gem compilation
+    "pkgconfig",
+    # ImageMagick C library
+    "libmagickwand",
+    # Font configuration
+    "fontconfig",
+    # A good fallback font
+    "dejavu_fonts",
+    # Arial-compatible fonts
+    "liberation_ttf",
+    # Font rendering
+    "freetype"
 ]
 
 [phases.install]