# frozen_string_literal: true require 'rails_helper' RSpec.describe ConversationReplyMailer do describe 'reply' do let!(:account) { create(:account) } let!(:agent) { create(:user, email: 'agent1@example.com', account: account) } let(:class_instance) { described_class.new } let(:email_channel) { create(:channel_email, account: account) } before do allow(described_class).to receive(:new).and_return(class_instance) allow(class_instance).to receive(:smtp_config_set_or_development?).and_return(true) end context 'with summary' do let(:conversation) { create(:conversation, account: account, assignee: agent) } let(:message) do create(:message, account: account, conversation: conversation, content_attributes: { cc_emails: 'agent_cc1@example.com', bcc_emails: 'agent_bcc1@example.com' }) end let(:new_message) do create(:message, account: account, conversation: conversation, content_attributes: { cc_emails: 'agent_cc2@example.com', bcc_emails: 'agent_bcc2@example.com' }) end let(:cc_message) do create(:message, account: account, message_type: :outgoing, conversation: conversation, content_attributes: { cc_emails: 'agent_cc1@example.com', bcc_emails: 'agent_bcc1@example.com' }) end let(:private_message) { create(:message, account: account, content: 'This is a private message', conversation: conversation) } let(:mail) { described_class.reply_with_summary(message.conversation, message.id).deliver_now } let(:cc_mail) { described_class.reply_with_summary(cc_message.conversation, message.id).deliver_now } it 'renders the default subject' do expect(mail.subject).to eq("[##{message.conversation.display_id}] New messages on this conversation") end it 'renders the subject in conversation as reply' do conversation.additional_attributes = { 'mail_subject': 'Mail Subject' } conversation.save! new_message.save! expect(mail.subject).to eq('Re: Mail Subject') end it 'not have private notes' do # make the message private private_message.private = true private_message.save! expect(mail.body.decoded).not_to include(private_message.content) expect(mail.body.decoded).to include(message.content) end it 'will not send email if conversation is already viewed by contact' do create(:message, message_type: 'outgoing', account: account, conversation: conversation) conversation.update(contact_last_seen_at: Time.zone.now) expect(mail).to be_nil end it 'will send email to cc and bcc email addresses' do expect(cc_mail.cc.first).to eq(cc_message.content_attributes[:cc_emails]) expect(cc_mail.bcc.first).to eq(cc_message.content_attributes[:bcc_emails]) end end context 'without assignee' do let(:conversation) { create(:conversation, assignee: nil) } let(:message) { create(:message, message_type: :outgoing, conversation: conversation) } let(:mail) { described_class.reply_with_summary(message.conversation, message.id).deliver_now } it 'has correct name' do expect(mail[:from].display_names).to eq(["#{message.sender.available_name} from #{message.conversation.inbox.sanitized_name}"]) end end context 'without summary' do let(:conversation) { create(:conversation, assignee: agent, account: account).reload } let(:message_1) { create(:message, conversation: conversation, account: account, content: 'Outgoing Message 1').reload } let(:message_2) { build(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Outgoing Message 2') } let(:private_message) do create(:message, content: 'This is a private message', conversation: conversation, account: account, message_type: 'outgoing').reload end let(:mail) { described_class.reply_without_summary(message_2.conversation, message_2.id).deliver_now } before do message_2.save! end it 'renders the default subject' do expect(mail.subject).to eq("[##{message_2.conversation.display_id}] New messages on this conversation") end it 'renders the subject in conversation' do conversation.additional_attributes = { 'mail_subject': 'Mail Subject' } conversation.save! expect(mail.subject).to eq('Mail Subject') end it 'not have private notes' do # make the message private private_message.private = true private_message.save! expect(mail.body.decoded).not_to include(private_message.content) end it 'onlies have the messages sent by the agent' do expect(mail.body.decoded).not_to include(message_1.content) expect(mail.body.decoded).to include(message_2.content) end it 'will not send email if conversation is already viewed by contact' do create(:message, message_type: 'outgoing', account: account, conversation: conversation) conversation.update(contact_last_seen_at: Time.zone.now) expect(mail).to be_nil end end context 'with references header' do let(:conversation) { create(:conversation, assignee: agent, inbox: email_channel.inbox, account: account).reload } let(:message) { create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Outgoing Message 2') } let(:mail) { described_class.email_reply(message).deliver_now } context 'when starting a new conversation' do let(:first_outgoing_message) do create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'First outgoing message') end let(:mail) { described_class.email_reply(first_outgoing_message).deliver_now } it 'has only the conversation reference' do # When starting a conversation, references will have the default conversation ID # Extract domain from the actual references header to handle dynamic domain selection actual_domain = mail.references.split('@').last expected_reference = "account/#{account.id}/conversation/#{conversation.uuid}@#{actual_domain}" expect(mail.references).to eq(expected_reference) end end context 'when replying to a message with no references' do let(:incoming_message) do create(:message, conversation: conversation, account: account, message_type: 'incoming', source_id: '', content: 'Incoming message', content_attributes: { 'email' => { 'message_id' => 'incoming-123@example.com' } }) end let(:reply_message) do create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Reply to incoming') end let(:mail) { described_class.email_reply(reply_message).deliver_now } before do incoming_message end it 'includes only the in_reply_to id in references' do # References should only have the incoming message ID when no prior references exist expect(mail.references).to eq('incoming-123@example.com') end end context 'when replying to a message that has references' do let(:incoming_message_with_refs) do create(:message, conversation: conversation, account: account, message_type: 'incoming', source_id: '', content: 'Incoming with references', content_attributes: { 'email' => { 'message_id' => 'incoming-456@example.com', 'references' => ['', ''] } }) end let(:reply_message) do create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Reply to message with refs') end let(:mail) { described_class.email_reply(reply_message).deliver_now } before do incoming_message_with_refs end it 'includes existing references plus the in_reply_to id' do # Rails returns references as an array when multiple values are present expected_references = ['ref-1@example.com', 'ref-2@example.com', 'incoming-456@example.com'] expect(mail.references).to eq(expected_references) end end end context 'with email reply' do let(:conversation) { create(:conversation, assignee: agent, inbox: email_channel.inbox, account: account).reload } let(:message) { create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Outgoing Message 2') } let(:mail) { described_class.email_reply(message).deliver_now } it 'renders the subject' do expect(mail.subject).to eq("[##{message.conversation.display_id}] New messages on this conversation") end it 'renders the body' do expect(mail.decoded).to include message.content end it 'builds messageID properly' do expect(mail.message_id).to eq("conversation/#{conversation.uuid}/messages/#{message.id}@#{conversation.account.domain}") end context 'when message is a CSAT survey' do let(:csat_message) do create(:message, conversation: conversation, account: account, message_type: 'template', content_type: 'input_csat', content: 'How would you rate our support?', sender: agent) end it 'includes CSAT survey URL in outgoing_content' do with_modified_env 'FRONTEND_URL' => 'https://app.chatwoot.com' do mail = described_class.email_reply(csat_message).deliver_now expect(mail.decoded).to include "https://app.chatwoot.com/survey/responses/#{conversation.uuid}" end end it 'uses outgoing_content for CSAT message body' do with_modified_env 'FRONTEND_URL' => 'https://app.chatwoot.com' do mail = described_class.email_reply(csat_message).deliver_now expect(mail.decoded).to include csat_message.outgoing_content end end end context 'with email attachments' do it 'includes small attachments as email attachments' do message_with_attachment = create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Message with small attachment') attachment = message_with_attachment.attachments.new(account_id: account.id, file_type: :file) attachment.file.attach(io: Rails.root.join('spec/assets/avatar.png').open, filename: 'avatar.png', content_type: 'image/png') attachment.save! mail = described_class.email_reply(message_with_attachment).deliver_now # Should be attached to the email expect(mail.attachments.map(&:filename).map(&:to_s)).to include('avatar.png') # Should not be in large_attachments expect(mail.body.encoded).not_to include('Attachments:') end it 'renders large attachments as links in the email body' do message_with_large_attachment = create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Message with large attachment') attachment = message_with_large_attachment.attachments.new(account_id: account.id, file_type: :file) attachment.file.attach(io: Rails.root.join('spec/assets/large_file.pdf').open, filename: 'large_file.pdf', content_type: 'application/pdf') attachment.save! mail = described_class.email_reply(message_with_large_attachment).deliver_now # Should NOT be attached to the email expect(mail.attachments.map(&:filename).map(&:to_s)).not_to include('large_file.pdf') # Should be rendered as a link in the body expect(mail.body.encoded).to include('Attachments:') expect(mail.body.encoded).to include('large_file.pdf') # Should render a link with large_file.pdf as the link text expect(mail.body.encoded).to match(%r{]*>large_file\.pdf}) # Small file should not be rendered as a link in the body expect(mail.body.encoded).not_to match(%r{]*>avatar\.png}) end it 'handles both small and large attachments correctly' do message_with_mixed_attachments = create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Message with mixed attachments') # Small attachment small_attachment = message_with_mixed_attachments.attachments.new(account_id: account.id, file_type: :file) small_attachment.file.attach(io: Rails.root.join('spec/assets/avatar.png').open, filename: 'avatar.png', content_type: 'image/png') small_attachment.save! # Large attachment large_attachment = message_with_mixed_attachments.attachments.new(account_id: account.id, file_type: :file) large_attachment.file.attach(io: Rails.root.join('spec/assets/large_file.pdf').open, filename: 'large_file.pdf', content_type: 'application/pdf') large_attachment.save! mail = described_class.email_reply(message_with_mixed_attachments).deliver_now # Small file should be attached expect(mail.attachments.map(&:filename).map(&:to_s)).to include('avatar.png') # Large file should NOT be attached expect(mail.attachments.map(&:filename).map(&:to_s)).not_to include('large_file.pdf') # Large file should be rendered as a link in the body expect(mail.body.encoded).to include('Attachments:') expect(mail.body.encoded).to include('large_file.pdf') # Should render a link with large_file.pdf as the link text expect(mail.body.encoded).to match(%r{]*>large_file\.pdf}) # Small file should not be rendered as a link in the body expect(mail.body.encoded).not_to match(%r{]*>avatar\.png}) end end context 'with custom email content' do it 'uses custom HTML content when available and creates multipart email' do message_with_custom_content = create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Regular message content', content_attributes: { email: { html_content: { reply: '

Custom HTML content for email

' }, text_content: { reply: 'Custom text content for email' } } }) mail = described_class.email_reply(message_with_custom_content).deliver_now # Check HTML part contains custom HTML content html_part = mail.html_part || mail expect(html_part.body.encoded).to include('

Custom HTML content for email

') expect(html_part.body.encoded).not_to include('Regular message content') # Check text part contains custom text content text_part = mail.text_part if text_part expect(text_part.body.encoded).to include('Custom text content for email') expect(text_part.body.encoded).not_to include('Regular message content') end end it 'falls back to markdown rendering when custom HTML content is not available' do message_without_custom_content = create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Regular **markdown** content') mail = described_class.email_reply(message_without_custom_content).deliver_now html_part = mail.html_part || mail expect(html_part.body.encoded).to include('markdown') expect(html_part.body.encoded).to include('Regular') end it 'handles empty custom HTML content gracefully' do message_with_empty_content = create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Regular **markdown** content', content_attributes: { email: { html_content: { reply: '' } } }) mail = described_class.email_reply(message_with_empty_content).deliver_now html_part = mail.html_part || mail expect(html_part.body.encoded).to include('markdown') expect(html_part.body.encoded).to include('Regular') end it 'handles nil custom HTML content gracefully' do message_with_nil_content = create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Regular **markdown** content', content_attributes: { email: { html_content: { reply: nil } } }) mail = described_class.email_reply(message_with_nil_content).deliver_now expect(mail.body.encoded).to include('markdown') expect(mail.body.encoded).to include('Regular') end it 'uses custom text content in text part when only text is provided' do message_with_text_only = create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Regular message content', content_attributes: { email: { text_content: { reply: 'Custom text content only' } } }) mail = described_class.email_reply(message_with_text_only).deliver_now text_part = mail.text_part if text_part expect(text_part.body.encoded).to include('Custom text content only') expect(text_part.body.encoded).not_to include('Regular message content') end end end end context 'when smtp enabled for email channel' do let(:smtp_channel) do create(:channel_email, smtp_enabled: true, smtp_address: 'smtp.gmail.com', smtp_port: 587, smtp_login: 'smtp@gmail.com', smtp_password: 'password', smtp_domain: 'smtp.gmail.com', account: account) end let(:conversation) { create(:conversation, assignee: agent, inbox: smtp_channel.inbox, account: account).reload } let(:message) { create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Outgoing Message 2') } it 'use smtp mail server' do mail = described_class.email_reply(message) expect(mail.delivery_method.settings.empty?).to be false expect(mail.delivery_method.settings[:address]).to eq 'smtp.gmail.com' expect(mail.delivery_method.settings[:port]).to eq 587 end it 'renders sender name in the from address' do mail = described_class.email_reply(message) expect(mail['from'].value).to eq "#{message.sender.available_name} from #{smtp_channel.inbox.sanitized_name} <#{smtp_channel.email}>" end it 'renders sender name even when assignee is not present' do conversation.update(assignee_id: nil) mail = described_class.email_reply(message) expect(mail['from'].value).to eq "#{message.sender.available_name} from #{smtp_channel.inbox.sanitized_name} <#{smtp_channel.email}>" end it 'renders assignee name in the from address when sender_name not available' do message.update(sender_id: nil) mail = described_class.email_reply(message) expect(mail['from'].value).to eq "#{conversation.assignee.available_name} from #{smtp_channel.inbox.sanitized_name} <#{smtp_channel.email}>" end it 'renders inbox name as sender and assignee or business_name not present' do message.update(sender_id: nil) conversation.update(assignee_id: nil) mail = described_class.email_reply(message) expect(mail['from'].value).to eq "Notifications from #{smtp_channel.inbox.sanitized_name} <#{smtp_channel.email}>" end context 'when friendly name enabled' do before do conversation.inbox.update(sender_name_type: 0) conversation.inbox.update(business_name: 'Business Name') end it 'renders sender name as sender and assignee and business_name not present' do message.update(sender_id: nil) conversation.update(assignee_id: nil) conversation.inbox.update(business_name: nil) mail = described_class.email_reply(message) expect(mail['from'].value).to eq "Notifications from #{conversation.inbox.sanitized_name} <#{smtp_channel.email}>" end it 'renders sender name as sender and assignee nil and business_name present' do message.update(sender_id: nil) conversation.update(assignee_id: nil) mail = described_class.email_reply(message) expect(mail['from'].value).to eq( "Notifications from #{conversation.inbox.business_name} <#{smtp_channel.email}>" ) end it 'renders sender name as sender nil and assignee and business_name present' do message.update(sender_id: nil) conversation.update(assignee_id: agent.id) mail = described_class.email_reply(message) expect(mail['from'].value).to eq "#{agent.available_name} from #{conversation.inbox.business_name} <#{smtp_channel.email}>" end it 'renders sender name as sender and assignee and business_name present' do agent_2 = create(:user, email: 'agent2@example.com', account: account) message.update(sender_id: agent_2.id) conversation.update(assignee_id: agent.id) mail = described_class.email_reply(message) expect(mail['from'].value).to eq "#{agent_2.available_name} from #{conversation.inbox.business_name} <#{smtp_channel.email}>" end end context 'when friendly name disabled' do before do conversation.inbox.update(sender_name_type: 1) conversation.inbox.update(business_name: 'Business Name') end it 'renders sender name as business_name not present' do message.update(sender_id: nil) conversation.update(assignee_id: nil) conversation.inbox.update(business_name: nil) mail = described_class.email_reply(message) expect(mail['from'].value).to eq "#{conversation.inbox.sanitized_name} <#{smtp_channel.email}>" end it 'renders sender name as business_name present' do message.update(sender_id: nil) conversation.update(assignee_id: nil) mail = described_class.email_reply(message) expect(mail['from'].value).to eq "#{conversation.inbox.business_name} <#{smtp_channel.email}>" end end end context 'when smtp enabled for microsoft email channel' do let(:ms_smtp_channel) do create(:channel_email, imap_login: 'smtp@outlook.com', imap_enabled: true, account: account, provider: 'microsoft', provider_config: { access_token: 'access_token' }) end let(:conversation) { create(:conversation, assignee: agent, inbox: ms_smtp_channel.inbox, account: account).reload } let(:message) { create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Outgoing Message 2') } it 'use smtp mail server' do mail = described_class.email_reply(message) expect(mail.delivery_method.settings.empty?).to be false expect(mail.delivery_method.settings[:address]).to eq 'smtp.office365.com' expect(mail.delivery_method.settings[:port]).to eq 587 end end context 'when smtp enabled for google email channel' do let(:ms_smtp_channel) do create(:channel_email, imap_login: 'smtp@gmail.com', imap_enabled: true, account: account, provider: 'google', provider_config: { access_token: 'access_token' }) end let(:conversation) { create(:conversation, assignee: agent, inbox: ms_smtp_channel.inbox, account: account).reload } let(:message) { create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Outgoing Message 2') } it 'use smtp mail server' do mail = described_class.email_reply(message) expect(mail.delivery_method.settings.empty?).to be false expect(mail.delivery_method.settings[:address]).to eq 'smtp.gmail.com' expect(mail.delivery_method.settings[:port]).to eq 587 end end context 'when smtp disabled for email channel', :test do let(:conversation) { create(:conversation, assignee: agent, inbox: email_channel.inbox, account: account).reload } let(:message) { create(:message, conversation: conversation, account: account, message_type: 'outgoing', content: 'Outgoing Message 2') } it 'use default mail server' do mail = described_class.email_reply(message) expect(mail.delivery_method.settings).to be_empty end end context 'when custom domain and email is not enabled' do let(:inbox) { create(:inbox, account: account) } let(:inbox_member) { create(:inbox_member, user: agent, inbox: inbox) } let(:conversation) { create(:conversation, assignee: agent, inbox: inbox_member.inbox, account: account) } let!(:message) { create(:message, conversation: conversation, account: account) } let(:mail) { described_class.reply_with_summary(message.conversation, message.id).deliver_now } let(:domain) { account.inbound_email_domain } it 'renders the receiver email' do expect(mail.to).to eq([message&.conversation&.contact&.email]) end it 'renders the reply to email' do expect(mail.reply_to).to eq([message&.conversation&.assignee&.email]) end it 'sets the correct custom message id' do expect(mail.message_id).to eq("conversation/#{conversation.uuid}/messages/#{message.id}@#{domain}") end it 'sets the correct in reply to id' do expect(mail.in_reply_to).to eq("account/#{conversation.account.id}/conversation/#{conversation.uuid}@#{domain}") end end context 'when inbox email address is available' do let(:inbox) { create(:inbox, account: account, email_address: 'noreply@chatwoot.com') } let(:conversation) { create(:conversation, assignee: agent, inbox: inbox, account: account) } let!(:message) { create(:message, conversation: conversation, account: account) } let(:mail) { described_class.reply_with_summary(message.conversation, message.id).deliver_now } it 'set reply to email address as inbox email address' do expect(mail.from).to eq([inbox.email_address]) expect(mail.reply_to).to eq([inbox.email_address]) end end context 'when the custom domain emails are enabled' do let(:account) { create(:account) } let(:conversation) { create(:conversation, assignee: agent, account: account).reload } let(:message) { create(:message, message_type: :outgoing, conversation: conversation, account: account, inbox: conversation.inbox) } let(:mail) { described_class.reply_with_summary(message.conversation, message.id).deliver_now } before do account = conversation.account account.domain = 'example.com' account.support_email = 'support@example.com' account.enable_features('inbound_emails') account.save! end it 'sets reply to email to be based on the domain' do reply_to_email = "reply+#{message.conversation.uuid}@#{conversation.account.domain}" reply_to = "#{message.sender.available_name} from #{conversation.inbox.sanitized_name} <#{reply_to_email}>" expect(mail['REPLY-TO'].value).to eq(reply_to) expect(mail.reply_to).to eq([reply_to_email]) end it 'sets the from email to be the support email' do expect(mail['FROM'].value).to eq("#{conversation.messages.last.sender.available_name} from Inbox <#{conversation.account.support_email}>") expect(mail.from).to eq([conversation.account.support_email]) end it 'sets the correct custom message id' do expect(mail.message_id).to eq("conversation/#{conversation.uuid}/messages/#{message.id}@#{conversation.account.domain}") end it 'sets the correct in reply to id' do expect(mail.in_reply_to).to eq("account/#{conversation.account.id}/conversation/#{conversation.uuid}@#{conversation.account.domain}") end end context 'when inbound email domain is not enabled' do let(:new_account) { create(:account, domain: nil) } let!(:email_channel) { create(:channel_email, account: new_account) } let!(:inbox) { create(:inbox, channel: email_channel, account: new_account) } let(:inbox_member) { create(:inbox_member, user: agent, inbox: inbox) } let(:conversation) { create(:conversation, assignee: agent, inbox: inbox_member.inbox, account: new_account) } let!(:message) { create(:message, conversation: conversation, account: new_account) } let(:mail) { described_class.reply_with_summary(message.conversation, message.id).deliver_now } let(:domain) { inbox.channel.email.split('@').last } it 'sets the correct custom message id' do expect(mail.message_id).to eq("conversation/#{conversation.uuid}/messages/#{message.id}@#{domain}") end it 'sets the correct in reply to id' do expect(mail.in_reply_to).to eq("account/#{conversation.account.id}/conversation/#{conversation.uuid}@#{domain}") end end end end