Duplication of Attachments - Outlook & Hubspot Sales Tracker

[IDA-CLE]

Hi everyone,

I’m hoping to get some advice on an issue we’re currently experiencing with HubSpot Sales when linked through Outlook.

Whenever we correspond within an email thread, HubSpot automatically re-uploads the same attachment every time someone replies. Over the course of a long conversation this results in multiple duplicate files being added to the contact and deal record, which becomes messy and time-consuming to clean up.

Apart from manually deleting each duplicate, has anyone found a way to prevent HubSpot from re-saving the same attachment on every reply?

Any tips or workaround would be greatly appreciated!

[RubenBurdin]

Hi @IDA-CLE , unfortunately you’ve hit a known limitation rather than a misconfiguration.

HubSpot treats each logged email reply as a new engagement, and attachments are re-processed every time that engagement is created. HubSpot doesn’t currently deduplicate attachments at the file level within an email thread, so from its point of view it’s doing exactly what it’s designed to do, even though the outcome is messy in long conversations.

There isn’t a native setting to say “only save this attachment once per thread” in the Outlook Sales extension today. Once attachments are logged, the only true cleanup option is manual deletion, which is why you’re seeing the Ideas post referenced by Bérangère.

In practice, teams usually reduce the pain with behavior and process tweaks rather than technical fixes. The most reliable ones I’ve seen are switching to cloud-hosted links (OneDrive or SharePoint) instead of file attachments for back-and-forth conversations, and being more selective about what gets logged to HubSpot once a deal is in later stages. Some teams also turn off automatic logging and rely on manual log or BCC for important messages only, but that’s a trade-off and can cause gaps if people forget.

If you want to make noise that actually leads somewhere, upvoting and adding concrete examples to the Ideas post is worth doing. Attachment handling tends to get prioritized when there’s a clear operational impact story behind it. Not the answer anyone wants, but you’re not missing a hidden toggle here. Hope this helps

[danmoyle · Accepted solution]

Great callout @IDA-CLE - and I'm glad @BérangèreL shared the feature request in Ideas. That's my go-to when something like this comes up. As far as I've seen and know, manual deletion is the standard fix. I thinik bulk tools in Data Management > Data Quality can help merge or deduplicate records post-upload, but I've not done that in your use case situation (we're a Google shop). 

A quick search for some workarounds netted me these suggestions, but they aren't best-case scenarios. 

• Disable automatic email logging temporarily via HubSpot settings > Integrations > Email integration, then re-enable to reset glitches, though this risks missing other logs.​
• In Outlook, remove attachments manually before replying or use cloud links (e.g., OneDrive/SharePoint) instead of re-attaching files to avoid uploads altogether.​
• Train teams to log emails selectively via manual BCC to HubSpot or forward without attachments, preserving thread context without duplicates.

For now, asking HubSpot for the power to manage this on our side as users is the best bet. 

[BérangèreL]

Hi @IDA-CLE and welcome, we are delighted to have you here! 🧡

Thanks for reaching out to the HubSpot Community and for sharing your valuable feedback! I've shared it internally.

I’ve noticed a similar idea already present in our Ideas Forum: Prevent attachments from duplicating, e.g. in deals.

To contribute, you can upvote the existing idea and share more details about your specific use case in the comments.

Now, let's consult our Top Experts: Hi @danmoyle, @CarolinaDeMares and @trevordjones can you think of a workaround to help @IDA-CLE, please?

Thanks so much and have a brilliant day!
Bérangère