My boss has email logging turned off, but I believe they still have the extension installed. The current workflow is:
Contact created > Lead created > Task to contact created (either via email if we have email or through LinkedIn) > Task is Completed and the Lead moves from New to Attempting.
I want an automation that will move from Attempting to Connected when they respond, or Attempting to Scheduled when someone books time with them (they used Outlook Scheduling, not HubSpot).
Any ideas?
Hey @AReyes22,
Thanks for posting in the Community!
I’d like to tag in some Community experts here to see what suggestions they may have on automating this set up. @karstenkoehler, @RomyFuchs1, and @RubenBurdin - do any of you have insight on best practices here?
Shane, Senior Community Moderator
Hi @AReyes22,
When you say that your boss has email logging turned off, do you mean that they choose to not log any sends they make through their Outlook? If so, the first automation (move to “Connected” when they respond) will not be possible. Unless you’ve enabled the setting to log all incoming emails for all users or unless your boss is logging emails and replies, HubSpot will not be able to notice a response - which means that no automation can be built based on that.
The second part, moving them to “Scheduled”, can work if your boss has their calendar connected: Connect your calendar to HubSpot
Meetings booked through Outlook scheduling where the recipients match contacts in the HubSpot CRM should sync automatically. (Meetings booked through a HubSpot meeting link would still be more reliable. For example, I recently learned that meetings exceeting 64kb will not sync into HubSpot.)
You could create a lead-based workflow that enrolls leads when they’re associated to a meeting where activity date is more than 0 days from now, then update the lead stage accordingly.
Let me know if you have any follow-up questions!
A workflow can only fire on something HubSpot has actually recorded, so both moves come down to getting the activity onto the record.
For Attempting > Connected: the reply has to be logged. With logging off, there’s no reply event for the workflow to enroll on. Reply logging needs either the connected inbox or the Sales extension/add-in (and the original outgoing email has to be logged), and whether incoming replies get logged follows your account-wide “log replies only” setting. Once that’s on, you can enroll on the reply activity (Last activity date or Recent sales email replied date updating, for example) and set Lead status to Connected.
For Attempting > Scheduled: a booking made outside HubSpot won’t reliably create a meeting on the record, so there’s nothing solid to trigger on. Switch that step to a HubSpot meetings scheduling link instead and the booking creates a meeting on the contact, which lets you use the “Meeting booked” enrollment trigger and then set the status to Scheduled.
The automation itself is the easy part once the reply and the booking actually flow through HubSpot.
Note: this reply was drafted with AI assistance and fact-checked by me for accuracy.
Max Buining
HubSpot CRM-specialist
Pipelines · Forecasting · Dashboards
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@MBuining using the “Last activity date” for this isn’t a good idea, as this will also update when a note is logged - which doesn’t constitute a connect.
You’re right, good catch. Last activity date is too broad, a logged note or any activity bumps it, so it’d fire false Connected moves.
Cleaner signal for an actual reply is “Recent Sales Email Replied Date” updating, since that only moves on a real reply to a tracked sales email, or a logged call with a Connected outcome. Even then it’s “they responded” rather than a guaranteed two-way connect, but far more reliable than Last activity date.
Appreciate the correction.
Max Buining
Independent HubSpot Consultant — Sales Hub, dashboards & pipelines

Occasionally AI-assisted, always human-checked.