New Outllook & Outlook Web | From text box doesn't show with one click

Question

Hello !

I have a question.

In new outlook or the web when i choose show from check box it shows me the other email address button but when i click it , sometimes i need to click 5 times to show me the from text box. is it a problem?

I tried reset or repair in outlook client but nothing change.

Thanks

Answer 1

Hello @Charalampopoulos Christoforos, 

Thank you for taking the time to share the additional details and follow up. I really appreciate it.

Based on your additional information, the behavior you experienced is most likely related to a temporary UI or cache-related issue in New Outlook / Outlook Web, where the “From” field does not consistently switch into the editable text box on the first click. New Outlook relies on web-based components, and occasionally those components can become desynchronized, especially after feature updates or policy refreshes in managed environments.

Your reinstall action likely cleared the underlying cached state, which explains why the From field is now responding correctly.

For future uses:

• If the issue reappears, testing in Outlook on the Web (private/incognito window) can quickly confirm whether the problem is cache- or profile-related.
• If it becomes reproducible again across devices or users in the same organization, it would be worth raising with your IT admin, as corporate network policies and update rings can sometimes influence client-side behavior.

For now, since the issue is resolved and working as expected, no further action is needed. If anything changes or the behavior returns, feel free to update the thread and I'll be happy to investigate further with you.

Thanks again for your detailed feedback and for confirming the resolution.

Answer 2

Hello @Charalampopoulos Christoforos, 

Good day! I hope you are doing well. 

I understand that when you enable Show From in New Outlook or Outlook Web, the From selector appears, but the editable From text box only shows after several clicks, sometimes up to 5 times. If you have any additional information, please don't hesitate to share.

Based on my research and testing results, this behavior is currently not listed as an official Microsoft‑documented issue. 

To help us provide the most accurate and effective solution for your missing section, could you share a bit more detail about your setup: 

• Could you check whether the issue also occurs in Classic Outlook? 
• Do you have any additional mailboxes, such as shared mailboxes or aliases, configured in your profile? 
• Does the issue occur in all browsers, and have you tried testing in a private/incognito window? 
• Are there any browser extensions installed that might interfere with UI elements? 
• Is the behavior consistent every time, or does it only happen intermittently? 
• Does the problem continue when you sign in on a different device? 
• Do you have multiple accounts signed in within Outlook? 
• Which operating system are you currently using? (For example: Windows 10, Windows 11, etc.) 
• Are you connected to your organization’s network, or are you using a personal/home network? 

This additional context will help us understand your environment and the steps already taken so we can tailor the guidance to resolve the issue effectively. 

In the meantime, here are some basic checks you can try: 

• Test the behavior in a private/incognito browser window to rule out cache issues. 
• Try another browser (Edge / Chrome / Firefox) to compare responsiveness. 
• Clear browser cache or app cache for Outlook Web, as UI elements load dynamically. 
• Test with different identities (primary mailbox vs. shared mailbox) to see whether delay occurs only when loading additional “Send As / Send on Behalf” identities. 

I apologize if I could not jump straight to a solution. I want to avoid suggesting anything that might be inaccurate or unhelpful. Once we have the details above, we’ll be able to assist you more effectively and guide you toward the right resolution. 

Looking forward to your response so we can get this sorted out for you together. 

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Answer 3

The described behavior (needing multiple clicks on Other email address before the From text box appears in New Outlook or Outlook on the web) is not documented in the provided context as a known issue.

From the available information, the only documented From-related Outlook desktop issues are:

• In some Insider builds of Outlook for Microsoft 365 desktop, the From drop-down could not be used at all when a POP/IMAP account was in the profile, which was fixed by updating Office to a newer build.
• A separate issue where selecting the From drop-down showed a “Retrieving templates from server” prompt, also fixed by updating Office.

For Outlook desktop (not New Outlook), when the From field does not behave correctly, the recommended action is to update Office to a build where the issue is fixed:

1. In Outlook desktop, go to File > Office Account > Update Options > Update Now to ensure the latest build is installed.
2. If using an Insider channel, consider switching to a non‑Insider channel such as Current Channel.

If the problem is only in New Outlook or Outlook on the web and persists after updating, this behavior is not covered in the provided documentation. In that case, using Classic Outlook (where the From field is stable and fully supported) is the most reliable workaround when precise From‑address control is required.

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References:

• Cannot select From account in email with Outlook Desktop
• Outlook prompts “Retrieving templates from server” after selecting the From field drop down