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Summary

Google Calendar invites ending up in Office 365 junk folders can be a frustrating issue, particularly when regular emails from the same sender are delivered without problems. This common problem often points to specific nuances in how Office 365 processes calendar invites, especially those containing .ics attachments, and how it assesses sender reputation and message content. While general email authentication might be correctly configured, calendar invites are subject to additional layers of filtering due to their unique structure and historical abuse by spammers. Troubleshooting requires examining factors beyond standard email deliverability, such as client-specific settings, the sender's overall sending practices, and the Spam Confidence Level (SCL) assigned by Microsoft.

What email marketers say

Email marketers often grapple with the nuances of how different email types are filtered, especially when comparing regular emails to calendar invites. The consensus suggests that while foundational email deliverability practices (like proper authentication) are crucial, calendar invites present unique challenges due to their interactive nature and the way they are often abused for spam or phishing. Marketers highlight that even minor inconsistencies in recipient configurations or sender reputation can trigger junk folder placement for these specific message types.

Marketer view

Email marketer from Email Geeks notes that Google Calendar invites with .ics attachments are going to Office 365 junk for some users, despite regular emails from the same sender not having issues.

18 Nov 2020 - Email Geeks

Marketer view

Email marketer from Email Geeks confirms that the sender's mailfrom and DKIM signing domains are aligned, leading them to question if the issue is reputation-related since regular emails are unaffected.

18 Nov 2020 - Email Geeks

What the experts say

Deliverability experts agree that the problem of Google Calendar invites landing in Office 365 junk is multi-faceted, often stemming from a combination of sender reputation, specific content characteristics of calendar invites (especially .ics files), and recipient-side filtering mechanisms. They emphasize that while standard email authentication is foundational, calendar invites are treated with increased scrutiny due to their history as a spam and phishing vector. Understanding the nuances of Office 365's filtering logic, including SCL scores and the impact of a p=none DMARC policy, is key.

Expert view

Deliverability expert from Email Geeks emphasizes that a p=none DMARC policy is not always harmless and can influence filtering decisions, suggesting checking client-specific configurations if the issue isn't universal.

18 Nov 2020 - Email Geeks

Expert view

Deliverability expert from Email Geeks states that Office 365 requires authentication to align, regardless of whether there is a DMARC record for the domain, a critical factor for inbox placement.

18 Nov 2020 - Email Geeks

What the documentation says

Official documentation from major email providers and security entities provides critical insights into how calendar invites are processed and filtered. These documents highlight the importance of email authentication (SPF, DKIM, DMARC), content filtering mechanisms (like SCL), and the recognition of calendar invites as a potential avenue for malicious activities. Understanding these documented behaviors is essential for diagnosing and resolving deliverability issues for Google Calendar invites in Office 365 environments.

Technical article

Microsoft documentation outlines that the Spam Confidence Level (SCL) is a key metric in Exchange Online Protection (EOP) and Microsoft Defender for Office 365, where higher SCL values indicate a greater likelihood of an email being spam and thus quarantined or moved to junk.

1 Jan 2024 - Microsoft Docs

Technical article

Microsoft documentation states that calendar invites containing attachments, such as .ics files, are subject to content-based filtering algorithms that assess for malicious indicators or spam-like patterns, even if the sender's reputation is otherwise good.

1 Jan 2024 - Microsoft Docs

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