Exploratory Google Calendar API integration

.ruby-version

@@ -1 +1 @@
-3.4.6
+3.4.8

Gemfile

@@ -1,6 +1,6 @@
 source "https://rubygems.org"
 
-ruby "3.4.6"
+ruby file: ".ruby-version"
 
 # Bundle edge Rails instead: gem "rails", github: "rails/rails", branch: "main"
 gem "rails", "~> 8.0.3"
@@ -20,6 +20,8 @@ gem "stimulus-rails"
 gem "jbuilder"
 # API wrapper for Strava
 gem "strava-ruby-client"
+# Google Calendar API
+gem "google-apis-calendar_v3"
 # Vector support for SQLite
 gem "sqlite-vec"
 # OpenAI wrapper

Gemfile.lock

@@ -105,6 +105,7 @@ GEM
     debug (1.11.0)
       irb (~> 1.10)
       reline (>= 0.3.8)
+    declarative (0.0.20)
     dotenv (3.1.8)
     drb (2.2.3)
     ed25519 (1.4.0)
@@ -117,6 +118,8 @@ GEM
       faraday-net_http (>= 2.0, < 3.5)
       json
       logger
+    faraday-follow_redirects (0.5.0)
+      faraday (>= 1, < 3)
     faraday-multipart (1.1.1)
       multipart-post (~> 2.0)
     faraday-net_http (3.4.1)
@@ -130,6 +133,28 @@ GEM
       raabro (~> 1.4)
     globalid (1.3.0)
       activesupport (>= 6.1)
+    google-apis-calendar_v3 (0.52.0)
+      google-apis-core (>= 0.15.0, < 2.a)
+    google-apis-core (1.0.2)
+      addressable (~> 2.8, >= 2.8.7)
+      faraday (~> 2.13)
+      faraday-follow_redirects (~> 0.3)
+      googleauth (~> 1.14)
+      mini_mime (~> 1.1)
+      representable (~> 3.0)
+      retriable (~> 3.1)
+    google-cloud-env (2.3.1)
+      base64 (~> 0.2)
+      faraday (>= 1.0, < 3.a)
+    google-logging-utils (0.2.0)
+    googleauth (1.16.2)
+      faraday (>= 1.0, < 3.a)
+      google-cloud-env (~> 2.2)
+      google-logging-utils (~> 0.1)
+      jwt (>= 1.4, < 4.0)
+      multi_json (~> 1.11)
+      os (>= 0.9, < 2.0)
+      signet (>= 0.16, < 2.a)
     hashdiff (1.2.0)
     hashie (5.0.0)
     i18n (1.14.7)
@@ -193,6 +218,7 @@ GEM
     mini_mime (1.1.5)
     minitest (5.25.5)
     msgpack (1.8.0)
+    multi_json (1.19.1)
     multi_xml (0.7.2)
       bigdecimal (~> 3.1)
     multipart-post (2.4.1)
@@ -242,6 +268,7 @@ GEM
     omniauth-rails_csrf_protection (1.0.2)
       actionpack (>= 4.2)
       omniauth (~> 2.0)
+    os (1.1.4)
     ostruct (0.6.3)
     parallel (1.27.0)
     parser (3.3.9.0)
@@ -314,6 +341,11 @@ GEM
     regexp_parser (2.10.0)
     reline (0.6.2)
       io-console (~> 0.5)
+    representable (3.2.0)
+      declarative (< 0.1.0)
+      trailblazer-option (>= 0.1.1, < 0.2.0)
+      uber (< 0.2.0)
+    retriable (3.2.1)
     rexml (3.4.1)
     rubocop (1.79.0)
       json (~> 2.3)
@@ -369,6 +401,11 @@ GEM
       rexml (~> 3.2, >= 3.2.5)
       rubyzip (>= 1.2.2, < 3.0)
       websocket (~> 1.0)
+    signet (0.21.0)
+      addressable (~> 2.8)
+      faraday (>= 0.17.5, < 3.a)
+      jwt (>= 1.5, < 4.0)
+      multi_json (~> 1.10)
     snaky_hash (2.0.3)
       hashie (>= 0.1.0, < 6)
       version_gem (>= 1.1.8, < 3)
@@ -416,12 +453,14 @@ GEM
     thruster (0.1.14-arm64-darwin)
     thruster (0.1.14-x86_64-linux)
     timeout (0.4.3)
+    trailblazer-option (0.1.2)
     tsort (0.2.0)
     turbo-rails (2.0.16)
       actionpack (>= 7.1.0)
       railties (>= 7.1.0)
     tzinfo (2.0.6)
       concurrent-ruby (~> 1.0)
+    uber (0.1.0)
     unicode-display_width (3.1.4)
       unicode-emoji (~> 4.0, >= 4.0.4)
     unicode-emoji (4.0.4)
@@ -458,6 +497,7 @@ DEPENDENCIES
   brakeman
   capybara
   debug
+  google-apis-calendar_v3
   image_processing (~> 1.2)
   importmap-rails
   jbuilder
@@ -491,7 +531,7 @@ DEPENDENCIES
   webmock
 
 RUBY VERSION
-   ruby 3.4.6p54
+   ruby 3.4.8p72
 
 BUNDLED WITH
    2.6.9

app/controllers/plans_controller.rb

@@ -1,5 +1,5 @@
 class PlansController < ApplicationController
-  before_action :set_plan, only: %i[ show edit update destroy processing_status edit_workouts update_workouts create_blank_schedule ]
+  before_action :set_plan, only: %i[ show edit update destroy processing_status edit_workouts update_workouts create_blank_schedule toggle_calendar_sync ]
 
   # GET /plans or /plans.json
   def index
@@ -108,6 +108,20 @@ def processing_status
     end
   end
 
+  # PATCH /plans/1/toggle_calendar_sync
+  def toggle_calendar_sync
+    unless Current.user.google_calendar_ready?
+      redirect_to @plan, alert: "Please connect your Google account first to enable calendar sync."
+      return
+    end
+
+    new_state = !@plan.calendar_sync_enabled?
+    @plan.update!(calendar_sync_enabled: new_state)
+
+    notice = new_state ? "Calendar sync enabled. Your workouts will be synced to Google Calendar." : "Calendar sync disabled."
+    redirect_to @plan, notice: notice
+  end
+
   private
     # Use callbacks to share common setup or constraints between actions.
     def set_plan

app/jobs/delete_calendar_event_job.rb

@@ -0,0 +1,20 @@
+class DeleteCalendarEventJob < ApplicationJob
+  queue_as :default
+
+  def perform(user_id, calendar_id, event_id)
+    user = User.find(user_id)
+
+    return unless user.has_google_access_token?
+    return if calendar_id.blank? || event_id.blank?
+
+    service = GoogleCalendarService.new(user)
+    service.delete_event(calendar_id, event_id)
+
+    Rails.logger.info "Deleted calendar event #{event_id}"
+  rescue GoogleCalendarService::AuthenticationError => e
+    Rails.logger.error "Google auth error deleting calendar event #{event_id}: #{e.message}"
+  rescue StandardError => e
+    Rails.logger.error "Error deleting calendar event #{event_id}: #{e.message}"
+    raise e
+  end
+end

app/jobs/remove_plan_calendar_events_job.rb

@@ -0,0 +1,23 @@
+class RemovePlanCalendarEventsJob < ApplicationJob
+  queue_as :default
+
+  def perform(plan_id)
+    plan = Plan.find(plan_id)
+    user = plan.user
+
+    unless user.has_google_access_token?
+      Rails.logger.warn "User #{user.id} has no Google credentials, skipping calendar event removal"
+      return
+    end
+
+    service = GoogleCalendarService.new(user)
+    service.remove_plan_events(plan)
+
+    Rails.logger.info "Removed calendar events for plan #{plan_id}"
+  rescue GoogleCalendarService::AuthenticationError => e
+    Rails.logger.error "Google auth error removing calendar events for plan #{plan_id}: #{e.message}"
+  rescue StandardError => e
+    Rails.logger.error "Error removing calendar events for plan #{plan_id}: #{e.message}"
+    raise e
+  end
+end

app/jobs/sync_plan_to_calendar_job.rb

@@ -0,0 +1,28 @@
+class SyncPlanToCalendarJob < ApplicationJob
+  queue_as :default
+
+  def perform(plan_id)
+    plan = Plan.find(plan_id)
+    user = plan.user
+
+    unless user.has_google_access_token?
+      Rails.logger.warn "User #{user.id} has no Google credentials, skipping calendar sync"
+      return
+    end
+
+    unless plan.calendar_sync_enabled?
+      Rails.logger.info "Calendar sync not enabled for plan #{plan.id}, skipping"
+      return
+    end
+
+    service = GoogleCalendarService.new(user)
+    service.sync_plan(plan)
+
+    Rails.logger.info "Successfully synced plan #{plan.id} to Google Calendar"
+  rescue GoogleCalendarService::AuthenticationError => e
+    Rails.logger.error "Google auth error syncing plan #{plan_id}: #{e.message}"
+  rescue StandardError => e
+    Rails.logger.error "Error syncing plan #{plan_id} to calendar: #{e.message}"
+    raise e
+  end
+end

app/jobs/update_calendar_event_job.rb

@@ -0,0 +1,23 @@
+class UpdateCalendarEventJob < ApplicationJob
+  queue_as :default
+
+  def perform(activity_id)
+    activity = Activity.find(activity_id)
+    plan = activity.plan
+
+    return unless plan&.calendar_sync_enabled?
+
+    user = plan.user
+    return unless user.has_google_access_token?
+
+    service = GoogleCalendarService.new(user)
+    service.update_event(activity)
+
+    Rails.logger.info "Updated calendar event for activity #{activity_id}"
+  rescue GoogleCalendarService::AuthenticationError => e
+    Rails.logger.error "Google auth error updating calendar event for activity #{activity_id}: #{e.message}"
+  rescue StandardError => e
+    Rails.logger.error "Error updating calendar event for activity #{activity_id}: #{e.message}"
+    raise e
+  end
+end

app/models/activity.rb

@@ -5,8 +5,35 @@ class Activity < ApplicationRecord
   belongs_to :user, optional: true
   has_many :strava_activities, dependent: :destroy
 
+  after_update :sync_calendar_event, if: :calendar_sync_needed?
+  before_destroy :enqueue_calendar_event_deletion
+
   # Returns the first matched or linked StravaActivity, if any
   def matched_strava_activity
     strava_activities.where(match_status: %w[matched linked]).first
   end
+
+  private
+
+  def calendar_sync_needed?
+    return false unless plan&.calendar_sync_enabled?
+    return false unless plan&.user&.has_google_access_token?
+
+    saved_change_to_distance? || saved_change_to_description? || saved_change_to_start_date_local?
+  end
+
+  def sync_calendar_event
+    UpdateCalendarEventJob.perform_later(id)
+  end
+
+  def enqueue_calendar_event_deletion
+    return unless google_calendar_event_id.present?
+    return unless plan&.calendar_sync_enabled?
+
+    user = plan&.user
+    return unless user&.has_google_access_token?
+    return unless user&.google_calendar_id.present?
+
+    DeleteCalendarEventJob.perform_later(user.id, user.google_calendar_id, google_calendar_event_id)
+  end
 end

app/models/plan.rb

@@ -1,5 +1,6 @@
 class Plan < ApplicationRecord
   after_create :process_uploaded_photos
+  after_update :sync_calendar_if_enabled
 
   enum :plan_type, { template: "template", custom: "custom" }
   enum :processing_status, { idle: "idle", queued: "queued", processing: "processing", completed: "completed", failed: "failed" }
@@ -30,13 +31,21 @@ def photos_are_images
     end
   end
 
-  private
-
   def process_uploaded_photos
     # Note that right now this is being called for all after_create calls
     return unless photos.attached?
 
     job = PlanPhotoProcessorJob.perform_later(self)
     update!(processing_status: "queued", job_id: job.job_id)
   end
+
+  def sync_calendar_if_enabled
+    return unless saved_change_to_calendar_sync_enabled?
+
+    if calendar_sync_enabled?
+      SyncPlanToCalendarJob.perform_later(id)
+    else
+      RemovePlanCalendarEventsJob.perform_later(id)
+    end
+  end
 end

app/models/user.rb

@@ -83,6 +83,22 @@ def strava_connected?
     strava_id.present?
   end
 
+  def google_connected?
+    google_uid.present?
+  end
+
+  def google_calendar_ready?
+    google_connected? && has_google_access_token?
+  end
+
+  def has_google_access_token?
+    # Use parameterized SQL to check for token presence without triggering ActiveRecord encryption
+    sql = self.class.sanitize_sql_array(
+      [ "SELECT 1 FROM users WHERE id = ? AND google_access_token IS NOT NULL AND google_access_token != ''", id ]
+    )
+    self.class.connection.select_value(sql).present?
+  end
+
   def link_strava!(auth)
     update!(
       strava_id: auth.uid,