This morning I tried out the free version of Perplexity for the first time. One thing I noticed was it had an Outlook Connector and I wanted to specifically see what that was about. I have heard about Perplexity but never actually tried it out. Usually, I try out the free version prior to trying out the paid version. One thing I have noticed is that the primary differences between the paid and unpaid versions are:
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- Not always available for the free or unpaid users – there are times when one cannot use the service during what is deemed peak times and must try again later
- Data set limitations on the size/amount of input one can upload/give to the unpaid version – forced to input less of a data set size or in smaller chunks with the free or unpaid version
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These free use limitations appear to apply to most of the AI systems I have tried out over time.
My First Perplexity Chat
So here is my first conversation (query/chat) with Perplexity:
I am interested in as much information as you can provide about your “Outlook Connector”. I run a very small website development business and am interested in the best method for grabbing email addresses and names attached to those where available from my older emails. I have Outlook folders containing current clients, prospective clients, and previous clients. I have access to my own mail servers and have a SmarterMail server in particular that I recently set up mailing lists on for this eventual purpose.
Perplexity’s Answer
Perplexity’s Outlook Connector integrates with Outlook.com and Outlook on the Web, allowing you to query and search your emails and primary calendar directly within Perplexity for enriched responses. It requires granting permissions for read/write access to mail, contacts, and calendars, with enterprise-grade security ensuring data isn’t used for AI training. Currently, it focuses on querying inboxes (e.g., “Summarize emails from yesterday”) rather than bulk extraction of addresses or names, though future updates may add sending emails or events.appypieautomate+1
Outlook Connector Details
This feature connects via Settings > Connectors in Perplexity: enable it, log in to your Microsoft account, grant permissions, and finish setup. It’s personal-level access, so others in your organization can’t query your data unless shared in threads; admins can disable it organization-wide. For your small business use, it won’t directly extract lists from folders but could help analyze client/prospect emails via natural language queries like “List emails from prospective clients.”
Extracting Addresses from Outlook Folders
Outlook’s built-in Export wizard lets you pull email addresses (From, To, CC, BCC) from specific folders into a CSV: select File > Open & Export > Import/Export > Export to a file > Comma Separated Values, map address fields, and finish. Tools like Kutools for Outlook or Email Address Collector automate this further, extracting to contacts, groups, or CSV while handling duplicates. Avoid manual copy-paste for large folders; export per folder (current clients, prospects, previous) for organization.
Importing to SmarterMail
SmarterMail supports importing contacts from CSV or vCard files: go to Contacts, select Import, choose your Outlook-exported CSV, resolve conflicts, and complete. Export multiple contacts at once via Select mode, then Actions > Export to CSV/vCard for backups or transfers. Since you have mail server access and mailing lists set up, upload CSVs directly to build lists from extracted client data.
Recommended Workflow
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Export addresses/names from each Outlook folder to separate CSVs using the wizard or a tool like Email Address Collector.extendoffice+1
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Clean the CSV in Excel (remove duplicates, add categories like “current client”).[ablebits]
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Import CSVs into SmarterMail Contacts, then create/update mailing lists from them.[help.smartertools]
This method is free, precise for your folders, and leverages your SmarterMail setup without third-party subscriptions beyond optional add-ins.support.microsoft+1