diff --git a/.github/ISSUE_TEMPLATE/bug-report.md b/.github/ISSUE_TEMPLATE/bug-report.md
deleted file mode 100644
index c0e804de5..000000000
--- a/.github/ISSUE_TEMPLATE/bug-report.md
+++ /dev/null
@@ -1,79 +0,0 @@
----
-name: Bug report
-about: Report a bug and help us improve
-title: ""
-labels: ""
-assignees: ""
----
-
-<!--
-
-Hi there! 👋
-
-Thanks for reporting a bug.
-
-Please search for existing issues before filing, as they may contain additional
-information about the problem and descriptions of workarounds. Provide as much
-information as you can, so that we can reproduce the issue. Otherwise, we may
-not be able to help diagnose the problem, and may close the issue as
-unreproducible or incomplete. For visual defects, please include screenshots to
-help us understand the issue.
--->
-
-## OS/Web Information
-
-- Web Browser:
-- Local OS:
-- Remote OS:
-- Remote Architecture:
-- `code-server --version`:
-
-## Steps to Reproduce
-
-1.
-2.
-3.
-
-## Expected
-
-<!-- What should happen? -->
-
-## Actual
-
-<!-- What actually happens? -->
-
-## Logs
-
-<!--
-First run code-server with at least debug logging (or trace to be really
-thorough) by setting the --log flag or the LOG_LEVEL environment variable. -vvv
-and --verbose are aliases for --log trace. For example:
-
-code-server --log debug
-
-Once this is done, replicate the issue you're having then collect logging
-information from the following places:
-
-    1. The most recent files from ~/.local/share/code-server/coder-logs.
-    2. The browser console.
-    3. The browser network tab.
-
-Additionally, collecting core dumps (you may need to enable them first) if
-code-server crashes can be helpful.
--->
-
-<!--
-If you're having issues with installation please include the installation logs
-i.e. the output of `yarn global add code-server` if you installed with `yarn`
- -->
-
-## Screenshot
-
-<!-- Ideally provide a screenshot, gif, video or screen recording. -->
-
-## Notes
-
-<!-- If you can reproduce the issue on vanilla VS Code,
-please file the issue at the VS Code repository instead. -->
-
-This issue can be reproduced in VS Code: Yes/No
diff --git a/.github/ISSUE_TEMPLATE/bug-report.yml b/.github/ISSUE_TEMPLATE/bug-report.yml
new file mode 100644
index 000000000..230c2e67c
--- /dev/null
+++ b/.github/ISSUE_TEMPLATE/bug-report.yml
@@ -0,0 +1,74 @@
+name: Bug report
+description: File a bug report
+title: "[Bug]: "
+labels: ["bug", "triage"]
+body:
+  - type: checkboxes
+    attributes:
+      label: Is there an existing issue for this?
+      description: Please search to see if an issue already exists for the bug you encountered.
+      options:
+        - label: I have searched the existing issues
+          required: true
+  - type: textarea
+    attributes:
+      label: OS/Web Information
+      description: |
+        examples:
+          - **Web Browser**: Chrome
+          - **Local OS**: macOS
+          - **Remote OS**: Ubuntu
+          - **Remote Architecture**: amd64
+          - **`code-server --version`**: 4.0.1
+      value: |
+        - Web Browser:
+        - Local OS:
+        - Remote OS:
+        - Remote Architecture:
+        - `code-server --version`:
+      render: markdown
+    validations:
+      required: false
+  - type: textarea
+    attributes:
+      label: Expected
+      description: What should happen?
+    validations:
+      required: true
+  - type: textarea
+    attributes:
+      label: Actual
+      description: What actually happens?
+    validations:
+      required: true
+  - type: textarea
+    id: logs
+    attributes:
+      label: Logs
+      description: Run code-server with the --verbose flag and then paste any relevant logs from the server, from the browser console and/or the browser network tab. For issues with installation, include installation logs (i.e. output of `yarn global add code-server`).
+  - type: textarea
+    attributes:
+      label: Screenshot/Video
+      description: Please include a screenshot, gif or screen recording of your issue.
+    validations:
+      required: false
+  - type: checkboxes
+    attributes:
+      label: Does this issue happen in VS Code?
+      description: Please try reproducing this issue in VS Code
+      options:
+        - label: I cannot reproduce this in VS Code.
+          required: true
+  - type: checkboxes
+    attributes:
+      label: Are you accessing code-server over HTTPS?
+      description: code-server relies on service workers for many features. Double-check that you are using HTTPS.
+      options:
+        - label: I am using HTTPS.
+          required: true
+  - type: textarea
+    attributes:
+      label: Notes
+      description: Please include any addition notes that will help us resolve this issue.
+    validations:
+      required: false
diff --git a/.github/ISSUE_TEMPLATE/config.yml b/.github/ISSUE_TEMPLATE/config.yml
index 2f567fce3..e24498346 100644
--- a/.github/ISSUE_TEMPLATE/config.yml
+++ b/.github/ISSUE_TEMPLATE/config.yml
@@ -1,8 +1,8 @@
 blank_issues_enabled: false
 contact_links:
-  - name: Question
-    url: https://github.com/cdr/code-server/discussions/new?category_id=22503114
+  - name: Question?
+    url: https://github.com/coder/code-server/discussions/new?category_id=22503114
     about: Ask the community for help on our GitHub Discussions board
-  - name: Chat
-    about: Need immediate help or just want to talk? Hop in our Slack
+  - name: code-server Slack Community
+    about: Need immediate help or just want to talk? Hop in our Slack. Note - this Slack is not actively monitored by code-server maintainers.
     url: https://cdr.co/join-community
diff --git a/.github/ISSUE_TEMPLATE/doc.md b/.github/ISSUE_TEMPLATE/doc.md
index ba63b11bd..510e479f4 100644
--- a/.github/ISSUE_TEMPLATE/doc.md
+++ b/.github/ISSUE_TEMPLATE/doc.md
@@ -1,7 +1,13 @@
 ---
 name: Documentation improvement
 about: Suggest a documentation improvement
-title: ""
+title: "[Docs]: "
 labels: "docs"
-assignees: ""
+assignees: "@jsjoeio"
 ---
+
+## What is your suggestion?
+
+## How will this improve the docs?
+
+## Are you interested in submitting a PR for this?
diff --git a/.github/ISSUE_TEMPLATE/feature-request.md b/.github/ISSUE_TEMPLATE/feature-request.md
index 3f7411eef..2f05a4f8b 100644
--- a/.github/ISSUE_TEMPLATE/feature-request.md
+++ b/.github/ISSUE_TEMPLATE/feature-request.md
@@ -1,13 +1,15 @@
 ---
 name: Feature request
-about: Suggest an idea
-title: ""
-labels: feature
+about: Suggest an idea to improve code-server
+title: "[Feat]: "
+labels: enhancement
 assignees: ""
 ---
 
-<!--
-Please search for existing issues before filing.
+## What is your suggestion?
 
-Please describe the feature as clearly as possible!
--->
+## Why do you want this feature?
+
+## Are there any workarounds to get this functionality today?
+
+## Are you interested in submitting a PR for this?
diff --git a/.github/ISSUE_TEMPLATE/release.md b/.github/ISSUE_TEMPLATE/release.md
deleted file mode 100644
index 2ca6b100b..000000000
--- a/.github/ISSUE_TEMPLATE/release.md
+++ /dev/null
@@ -1,16 +0,0 @@
----
-name: Release
-about: "*For maintainers only*"
-title: "release: 0.0.0"
-labels: ""
-assignees: "@cdr/code-server-reviewers"
----
-
-<!-- Maintainer: fill out the checklist -->
-
-## Checklist
-
-- [ ] Assign to next release manager
-- [ ] Close previous release milestone
-- [ ] Create next release milestone
-- [ ] Associate issue with next release milestone