Skip to content

Register now for our Web Enablement Ecosystem webinar!

  • Contact us: +34 944 58 06 58
  • Plesk Partner Program
  • Plesk Lifecycle Policy
  • Blog
  • Contact us
  • Plesk 360
  • Contact us: +34 944 58 06 58
  • Plesk Partner Program
  • Plesk Lifecycle Policy
  • Blog
  • Contact us
  • Plesk 360
  • Solutions
    By Role
    • Developers
    • Content Managers
    • Digital Agencies
    • IT Admins
    • Web Hosters
    • Hyperscalers
    • Developers
    • Content Managers
    • Digital Agencies
    • IT Admins
    • Web Hosters
    • Hyperscalers
    By Edition
    • Web Admin Edition
    • Web Pro Edition
    • Web Host Edition
    • Business & Collaboration
    • Plesk WP Edition
    • Web Admin Edition
    • Web Pro Edition
    • Web Host Edition
    • Business & Collaboration
    • Plesk WP Edition
    By Cloud
    • Amazon Web Services
    • Microsoft Azure
    • Alibaba Cloud
    • GCP Marketplace
    • Vultr
    • DigitalOcean
    • Linode
    • UpCloud
    • Amazon Web Services
    • Microsoft Azure
    • Alibaba Cloud
    • GCP Marketplace
    • Vultr
    • DigitalOcean
    • Linode
    • UpCloud
    Partner Program
    Exclusive discounts, benefits and exposure to take your business to the next level
    Become a partner
    • By Role
      • Developers
      • Content Managers
      • Digital Agencies
      • IT Admins
      • Web Hosters
      • Hyperscalers
    • By Edition
      • Web Admin Edition
      • Web Pro Edition
      • Web Host Edition
      • Business & Collaboration
      • WP Edition
    • By Cloud
      • Amazon Web Services
      • Microsoft Azure
      • Alibaba Cloud
      • GCP Marketplace
      • Vultr
      • DigitalOcean
      • Linode
      • UpCloud
    • Partner Program
      • Partner Program
  • Product
    Explore Features
    • Everyone
    • Admins & Web Hosters
    • Developers
    • Designers & Agencies
    • Plesk Features
    • Everyone
    • Admins & Web Hosters
    • Developers
    • Designers & Agencies
    • Plesk Features
    Key Topics
    • SocialBee
    • WP Toolkit
    • Sitejet Builder
    • SEO Toolkit
    • Joomla! Toolkit
    • Plesk Premium Email
    • Plesk Email Security
    • SocialBee
    • WP Toolkit
    • Sitejet Builder
    • SEO Toolkit
    • Joomla! Toolkit
    • Plesk Premium Email
    • Plesk Email Security
    Feature Packs
    • Business & Collaboration
    • WP Pack
    • Hosting Pack
    • Power Pack
    • Language Pack
    • Business & Collaboration
    • WP Pack
    • Hosting Pack
    • Power Pack
    • Language Pack
    Featured Extension
    SocialBee
    • Explore Features
      • Everyone
      • Admins & Web Hosters
      • Developers
      • Designers & Agencies
      • Plesk Features
    • Key Topics
      • SocialBee
      • WP Toolkit
      • Sitejet Builder for Plesk
      • SEO Toolkit
      • Plesk Premium Email
      • Plesk Email Security
    • Feature Packs
      • Business & Collaboration
      • WP Pack
      • Hosting Pack
      • Power Pack
      • Language Pack
    • Featured Extension
      • Extension
  • Pricing
  • Extensions
  • Help Center
  • More
    • Careers
    • Events
    • Plesk University
  • FREE TRIAL
  • Solutions
    • By Role
      • Developers
      • Content Managers
      • Digital Agencies
      • IT Admins
      • Web Hosters
      • Hyperscalers
    • By Edition
      • Web Admin Edition
      • Web Pro Edition
      • Web Host Edition
      • Business & Collaboration
      • WP Edition
    • By Cloud
      • Amazon Web Services
      • Microsoft Azure
      • Alibaba Cloud
      • GCP Marketplace
      • Vultr
      • DigitalOcean
      • Linode
      • UpCloud
    • Partner Program
      • Partner Program
  • Product
    • Explore Features
      • Everyone
      • Admins & Web Hosters
      • Developers
      • Designers & Agencies
      • Plesk Features
    • Key Topics
      • SocialBee
      • WP Toolkit
      • Sitejet Builder
      • SEO Toolkit
      • Joomla! Toolkit
      • Plesk Premium Email
      • Plesk Email Security
    • Feature Packs
      • Business & Collaboration
      • WP Pack
      • Hosting Pack
      • Power Pack
      • Language Pack
    • Featured Extension
      • SocialBee
  • Pricing
  • Extensions
  • Help center
  • More
    • Careers
    • Events
    • Plesk University
    • Blog
    • Plesk Partner Program
    • Contact Us
  • FREE TRIAL
  • Solutions
    • By Role
      • Developers
      • Content Managers
      • Digital Agencies
      • IT Admins
      • Web Hosters
      • Hyperscalers
    • By Edition
      • Web Admin Edition
      • Web Pro Edition
      • Web Host Edition
      • Business & Collaboration
      • WP Edition
    • By Cloud
      • Amazon Web Services
      • Microsoft Azure
      • Alibaba Cloud
      • GCP Marketplace
      • Vultr
      • DigitalOcean
      • Linode
      • UpCloud
    • Partner Program
      • Partner Program
  • Product
    • Explore Features
      • Everyone
      • Admins & Web Hosters
      • Developers
      • Designers & Agencies
      • Plesk Features
    • Key Topics
      • SocialBee
      • WP Toolkit
      • Sitejet Builder
      • SEO Toolkit
      • Joomla! Toolkit
      • Plesk Premium Email
      • Plesk Email Security
    • Feature Packs
      • Business & Collaboration
      • WP Pack
      • Hosting Pack
      • Power Pack
      • Language Pack
    • Featured Extension
      • SocialBee
  • Pricing
  • Extensions
  • Help center
  • More
    • Careers
    • Events
    • Plesk University
    • Blog
    • Plesk Partner Program
    • Contact Us
  • FREE TRIAL

Knowledge Base

On Plesk for Windows server, Let’s Encrypt SSL certificate can not be issued for all domains with error 404: The filename, directory name, or volume label syntax is incorrect

 
domainshttphttpsletsencryptmicrosoft

Symptoms

  • On a Plesk for Windows server, issuing Let's Encrypt certificate on all domains in Plesk fails:

    Error: Error: Could not issue a Let's Encrypt SSL/TLS certificate for example.com.
    The authorization token is not available at http://example.com/.well-known/acme-challenge/.
    To resolve the issue, make it is possible to download the token file via the above URL.
    See the related Knowledge Base article for details.
    Additional error details:
    Invalid response from https://acme-v01.api.letsencrypt.org/acme/authz/_oRgI1kwh53Fr07VRtI-55Zj7NqY75KI5e41PCsQqow.
    Details:
    Type: urn:acme:error:unauthorized
    Status: 403
    Detail: Invalid response from http://example.com/.well-known/acme-challenge/uxIoK_7-BjsuBu362yQ_QD5ovykddVeyKEgfEAre9P8: "
    HTTP Error 404.0 - Not Found
    The resource you are looking for has been removed, had its name changed, or is temporarily unavailable

  • Accessing the authorization token on the URL from the error http://example.com/.well-known/acme-challenge/uxIoK_7-BjsuBu362yQ_QD5ovykddVeyKEgfEAre9P8 in a browser fails with the error 404.4.

Cause

The IIS module ApplicationRequestRouting is not enabled/installed or corrupted at Internet Information Services (IIS) Manager > server_hostname > Modules.

The following output is provided when accessing the link from the error message with enabled Failed Request Tracing:

ModuleName IIS Web Core
Notification MAP_REQUEST_HANDLER
HttpStatus 404
HttpReason Not Found
HttpSubStatus 4
ErrorCode The filename, directory name, or volume label syntax is incorrect.

Resolution

  1. Connect to the server using RDP.

  2. Download and install Application Request Routing package from Microsoft website:

    • Microsoft Application Request Routing 3.0 (x64).

    • Microsoft Application Request Routing 3.0 (x86).

  3. Reboot the server.

Tweet
Share
Share
Email
0 Shares
Read the full article
Related Posts

Exploring Plesk’s Added Value Solutions So Far in 2023

Read More »

Unveiling Sitejet Builder: The Perfect Match for Your Effortless Website Creation Needs

Read More »

Dynamic List vs. Active List: A Comprehensive Comparison – Unveiling the Ultimate Winner!

Read More »
Knowledge Base

Unable to install a Let’s Encrypt certificate for a domain in Plesk for Windows: 404 Not Found

Read More »

How to customize Plesk URL

Read More »

 How to enable redirection from HTTP to HTTPS for a domain in Plesk

Read More »

Unable to issue a Let’s Encrypt certificate: The token file is either unreadable or does not have the read permission

Read More »

Hosting Wiki

  • Server Redundancy
  • Bare Metal Server
  • Oracle VM Server
  • Server Virtualization Software
  • Windows Server
  • HTTP/3
  • HTTP/2
  • Domain
  • Plesk
  • Lighttpd
  • Web Server
  • DNS Server
  • SSL
  • URL
  • HTTP

Industry
Partners

industry-partner_ALIBABA
industry-partner_GOOGLEPARTNER
industry-partner_MICROSOFT
industry-partner_REDHAT-r2
industry-partner_ALIBABA
industry-partner_AUTOMATTIC
industry-partner_AWS
industry-partner_DIGITALOCEAN
industry-partner_SCALEWAY
Follow us:
Facebook Twitter Linkedin Youtube Github

COMPANY

About Plesk
Our Brand
Legal
Careers
Impressum

PRODUCT

Pricing 
Extensions
What’s new

KNOWLEDGE BASE

Documentation
Help Center
Migrate to Plesk
Contact Us
Hosting Wiki
Preview releases

PROGRAMS

Contributor Program NEW
Partner Program
Affiliate ProgramNEW

COMMUNITY

Blog
Forums 
Plesk University

First defaul

Company

About Plesk
Our Brand
Legal
Careers
Impressum

PRODUCT

Pricing 
Extensions
What’s new

KNOWLEDGE BASE​

Documentation
Help Center
Migrate to Plesk
Contact Us
Hosting Wiki
Preview releases

PROGRAMS​

Contributor Program NEW
Partner Program
Affiliate ProgramNEW

COMMUNITY​

Blog
Forums
Plesk University

Follow us:
Facebook Twitter Linkedin Youtube Github

© 2025 WebPros International GmbH. All rights reserved. Plesk and the Plesk logo are trademarks of WebPros International GmbH.

Managed with love with Plesk WP Toolkit