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My Job Application Cover Letter emails are flagged as spam by most corporations

Brad Blonkvist 0 Reputation points
2026-01-23T15:29:34.12+00:00

Hello - I've been applying to jobs and following up with a cover letter and my resume. Often I don't know the email address of the HR person or likely boss I am writing to. I google the email syntax for the company and try to send them my cover letter. Often I'll get a bounce back saying their is no known receipient and then I'll try to send the cover letter again to a different email syntax. That's not the problem and I've been doing that 5-10 emails a day for a long long time.

However, in the last week, I've started getting bounce-back messages that state my email was deemed spam. This is happening across a wide range of companies and I think my emails are being labelled as spam by Microsoft network/software and not just a single company. What can I do about this? I'm just trying to find a job!! Thanks so much

Brad

Outlook | Windows | Classic Outlook for Windows | For home
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  1. EmilyS726 236K Reputation points Independent Advisor
    2026-01-23T16:02:53.38+00:00

    Can you use the instruction here, change the email to plain text or rich text format (basically avoid the html format) and see if it goes through:

    https://support.microsoft.com/office/change-the-message-format-to-html-rich-text-format-or-plain-text-in-outlook-338a389d-11da-47fe-b693-cf41f792fefa

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  2. AI answer

    2026-01-23T15:29:45.7866667+00:00

    It sounds like you're encountering issues with your emails being flagged as spam, which can be frustrating while job hunting. Here are some best practices you can follow to help ensure your emails are delivered successfully:

    1. Use a Professional Email Address: Ensure that your email address looks professional and is associated with a reputable domain. Avoid using free email services if possible.
    2. Check Your Email Content: Avoid using language or formatting that might trigger spam filters. This includes excessive use of exclamation marks, all caps, or certain keywords that are commonly associated with spam.
    3. Avoid Sending to Invalid Addresses: If you receive bounce-back messages indicating that an email address is invalid, make sure to remove those addresses from your list. Sending to invalid addresses can hurt your sending reputation.
    4. Authenticate Your Domain: If you're using a custom domain, ensure that it is properly authenticated with SPF, DKIM, and DMARC records. This helps improve your email deliverability.
    5. Limit the Number of Emails Sent: Sending too many emails in a short period can trigger spam filters. Try to space out your applications and follow-ups.
    6. Use a Reliable Email Service: Consider using a professional email service that can help manage your emails and improve deliverability.
    7. Monitor Your Sending Reputation: Use tools like Outlook's Smart Network Data Services (SNDS) to monitor your sending reputation and identify any issues.

    By following these practices, you can improve the chances of your emails being delivered successfully and not being flagged as spam.

    References:

    AI-generated content may be incorrect. Read our transparency notes for more information.

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