Configuring preferences and options in Outlook on the web for business
Hi Jason,
This is a known pain point with Outlook Web / new Outlook: images embedded inline in a signature (base64 data or local attachments) often get stripped or stop rendering once the signature is saved and reused, especially across different Outlook clients (desktop, web, mobile) and when a recipient's client blocks embedded content by default.
The fix that has worked consistently for me: host the logo/image at a permanent, publicly-accessible HTTPS URL (not a local file or an embedded attachment) and reference it with a standard img src="https://..." tag. That way every client just fetches the image from the web instead of depending on how each app handles embedded content. Worth checking the raw HTML your signature editor generates - if it's using base64 image data or a cid: reference instead of a real https:// URL, that is almost always the root cause.
If it helps, I built a free checker at signatureforever.com/en/check - you paste your signature HTML and it flags exactly this kind of issue (embedded vs. hosted images) plus other things that break across Outlook desktop/web, Gmail and Apple Mail. Full disclosure, it is my own tool, but the check itself is free and needs no signup.
Hope that gets the image showing consistently for you.