diff --git a/.github/scripts/draft-change-log-entries.sh b/.github/scripts/draft-change-log-entries.sh
index 7ebb9448355d..885d14498ad0 100755
--- a/.github/scripts/draft-change-log-entries.sh
+++ b/.github/scripts/draft-change-log-entries.sh
@@ -28,6 +28,17 @@ echo
 echo "### Migration notes"
 echo
 echo
+
+# Add breaking changes and deprecations sections
+if [[ -z $range ]]; then
+  labeled_range="HEAD"
+else
+  labeled_range="$range"
+fi
+
+"$(dirname "$0")/extract-labeled-prs.sh" "$labeled_range"
+echo
+
 echo "### 🌟 New javaagent instrumentation"
 echo
 echo
diff --git a/.github/scripts/extract-labeled-prs.sh b/.github/scripts/extract-labeled-prs.sh
new file mode 100755
index 000000000000..e01dbacb9eb9
--- /dev/null
+++ b/.github/scripts/extract-labeled-prs.sh
@@ -0,0 +1,78 @@
+#!/bin/bash -e
+
+# This script extracts PRs with "breaking change" and "deprecation" labels for the given version range
+# Usage: extract-labeled-prs.sh [git-range]
+# If no range is provided, it uses HEAD
+
+range="${1:-HEAD}"
+
+if [[ "$range" == "HEAD" ]]; then
+  # Get all commits from HEAD
+  commits=$(git log --reverse --pretty=format:"%H %s" HEAD)
+else
+  # Get commits in the specified range
+  commits=$(git log --reverse --pretty=format:"%H %s" "$range")
+fi
+
+# Initialize tracking variables
+breaking_changes=""
+deprecations=""
+breaking_changes_found=false
+deprecations_found=false
+
+# Process each commit to find PRs with specified labels
+while IFS= read -r line; do
+  if [[ -z "$line" ]]; then
+    continue
+  fi
+
+  # Extract PR number from commit message
+  if [[ $line =~ \(#([0-9]+)\)$ ]]; then
+    pr_number="${BASH_REMATCH[1]}"
+    commit_subject=$(echo "$line" | cut -d' ' -f2- | sed 's/ (#[0-9]*)$//')
+
+    # Get PR labels using GitHub CLI
+    if pr_labels=$(gh pr view "$pr_number" --json labels --jq '.labels[].name' 2>/dev/null); then
+      # Check for breaking change label
+      if echo "$pr_labels" | grep -q "^breaking change$"; then
+        breaking_changes_found=true
+        breaking_changes+="- $commit_subject"$'\n'"  ([#$pr_number](https://github.com/open-telemetry/opentelemetry-java-instrumentation/pull/$pr_number))"$'\n'$'\n'
+      fi
+
+      # Check for deprecation label
+      if echo "$pr_labels" | grep -q "^deprecation$"; then
+        deprecations_found=true
+        deprecations+="- $commit_subject"$'\n'"  ([#$pr_number](https://github.com/open-telemetry/opentelemetry-java-instrumentation/pull/$pr_number))"$'\n'$'\n'
+      fi
+    fi
+  fi
+done <<< "$commits"
+
+# Output breaking changes section
+if [[ "$breaking_changes_found" == "true" ]]; then
+  echo "### ⚠️ Breaking Changes"
+  echo
+  echo -n "$breaking_changes"
+fi
+
+# Output deprecations section
+if [[ "$deprecations_found" == "true" ]]; then
+  echo "### 🚫 Deprecations"
+  echo
+  echo -n "$deprecations"
+fi
+
+# Output "no changes" messages if needed
+if [[ "$breaking_changes_found" == "false" ]]; then
+  echo "### ⚠️ Breaking Changes"
+  echo
+  echo "*No breaking changes in this release.*"
+  echo
+fi
+
+if [[ "$deprecations_found" == "false" ]]; then
+  echo "### 🚫 Deprecations"
+  echo
+  echo "*No deprecations in this release.*"
+  echo
+fi
diff --git a/.github/scripts/format-release-notes.sh b/.github/scripts/format-release-notes.sh
new file mode 100755
index 000000000000..68a7cd08f8ef
--- /dev/null
+++ b/.github/scripts/format-release-notes.sh
@@ -0,0 +1,57 @@
+#!/bin/bash -e
+
+# Format changelog section for GitHub release notes
+# Usage: format-release-notes.sh <changelog_section_file> <output_file>
+
+changelog_section="$1"
+output_file="$2"
+
+if [[ -z "$changelog_section" || -z "$output_file" ]]; then
+  echo "Usage: format-release-notes.sh <changelog_section_file> <output_file>"
+  exit 1
+fi
+
+if [[ ! -f "$changelog_section" ]]; then
+  echo "Error: Changelog section file '$changelog_section' not found"
+  exit 1
+fi
+
+{
+  # Add breaking changes section if it exists
+  if grep -q "### ⚠️ Breaking Changes" "$changelog_section"; then
+    cat << 'EOF'
+
+## 🚨 IMPORTANT: Breaking Changes
+
+This release contains breaking changes. Please review the changes below:
+
+EOF
+
+    # Extract breaking changes section, format for release notes
+    sed -n '/### ⚠️ Breaking Changes/,/^### /p' "$changelog_section" | sed '$d' | \
+      perl -0pe 's/(?<!\n)\n *(?!\n)(?![-*] )(?![1-9]+\. )/ /g'
+
+    echo -e "\n---\n"
+  fi
+
+  # Add deprecations section if it exists
+  if grep -q "### 🚫 Deprecations" "$changelog_section"; then
+    cat << 'EOF'
+
+## 🚫 Deprecations
+
+This release includes deprecations. Please review the changes below and plan for future updates:
+
+EOF
+
+    # Extract deprecations section, format for release notes
+    sed -n '/### 🚫 Deprecations/,/^### /p' "$changelog_section" | sed '$d' | \
+      perl -0pe 's/(?<!\n)\n *(?!\n)(?![-*] )(?![1-9]+\. )/ /g'
+
+    echo -e "\n---\n"
+  fi
+
+  # the complex perl regex is needed because markdown docs render newlines as soft wraps
+  # while release notes render them as line breaks
+  perl -0pe 's/(?<!\n)\n *(?!\n)(?![-*] )(?![1-9]+\. )/ /g' "$changelog_section"
+} > "$output_file"
diff --git a/.github/workflows/pr-automation-comments.yml b/.github/workflows/pr-automation-comments.yml
new file mode 100644
index 000000000000..d7f012bef972
--- /dev/null
+++ b/.github/workflows/pr-automation-comments.yml
@@ -0,0 +1,112 @@
+name: PR Automation Comments
+on:
+  pull_request:
+    types: [labeled]
+
+permissions:
+  pull-requests: write
+
+jobs:
+  comment-on-breaking-change:
+    if: contains(github.event.label.name, 'breaking change')
+    runs-on: ubuntu-latest
+    steps:
+      - name: Comment on PR
+        uses: actions/github-script@v7
+        with:
+          script: |
+            const { data: comments } = await github.rest.issues.listComments({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              issue_number: context.issue.number,
+            });
+
+            // Check if we've already commented about breaking changes
+            const botComment = comments.find(comment => 
+              comment.user.login === 'github-actions[bot]' && 
+              comment.body.includes('⚠️ Breaking Change Documentation Required')
+            );
+
+            if (!botComment) {
+              const commentBody = [
+                "## ⚠️ Breaking Change Documentation Required",
+                "",
+                "This PR has been labeled as a **breaking change**. Please ensure you provide the following information:",
+                "",
+                "### Migration Notes Required",
+                "Please add detailed migration notes to help users understand:",
+                "- What is changing and why",
+                "- How to update their code/configuration", 
+                "- Any alternative approaches if applicable",
+                "- Code examples showing before/after usage",
+                "",
+                "### Checklist",
+                "- [ ] Migration notes added to the PR description",
+                "- [ ] Breaking change is documented in the changelog entry for the next release",
+                "- [ ] Consider if this change requires a major version bump",
+                "",
+                "Your migration notes will be included in the release notes to help users upgrade smoothly. The more detailed and helpful they are, the better the user experience will be.",
+                "",
+                "---",
+                "*This comment was automatically generated because the `breaking change` label was applied to this PR.*"
+              ].join("\n");
+
+              await github.rest.issues.createComment({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                issue_number: context.issue.number,
+                body: commentBody
+              });
+            }
+
+  comment-on-deprecation:
+    if: contains(github.event.label.name, 'deprecation')
+    runs-on: ubuntu-latest
+    steps:
+      - name: Comment on PR
+        uses: actions/github-script@v7
+        with:
+          script: |
+            const { data: comments } = await github.rest.issues.listComments({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              issue_number: context.issue.number,
+            });
+
+            // Check if we've already commented about deprecation
+            const botComment = comments.find(comment => 
+              comment.user.login === 'github-actions[bot]' && 
+              comment.body.includes('📋 Deprecation Notice')
+            );
+
+            if (!botComment) {
+              const commentBody = [
+                "## 📋 Deprecation Notice",
+                "",
+                "This PR has been labeled as a **deprecation**. Please ensure you provide the following information:",
+                "",
+                "### 📝 Deprecation Details Required",
+                "Please add details to help users understand:",
+                "- What is being deprecated and why",
+                "- What should be used instead (if applicable)",
+                "- Timeline for removal (if known)",
+                "- Any migration guidance",
+                "",
+                "### 📋 Checklist",
+                "- [ ] Deprecation details added to the PR description",
+                "- [ ] Deprecation is documented in the changelog entry for the next release",
+                "- [ ] Consider adding deprecation warnings in code/documentation",
+                "",
+                "Your deprecation notes will be included in the release notes to help users prepare for future changes.",
+                "",
+                "---",
+                "*This comment was automatically generated because the `deprecation` label was applied to this PR.*"
+              ].join("\n");
+
+              await github.rest.issues.createComment({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                issue_number: context.issue.number,
+                body: commentBody
+              });
+            }
diff --git a/.github/workflows/pr-label-automation.yml b/.github/workflows/pr-label-automation.yml
new file mode 100644
index 000000000000..341c95ba2668
--- /dev/null
+++ b/.github/workflows/pr-label-automation.yml
@@ -0,0 +1,173 @@
+name: PR Label Automation
+on:
+  issue_comment:
+    types: [created]
+
+permissions:
+  contents: read
+  issues: write
+  pull-requests: write
+
+jobs:
+  auto-label:
+    # Only run on pull request comments
+    if: github.event.issue.pull_request != null
+    runs-on: ubuntu-latest
+    steps:
+      - name: Add breaking change label
+        if: github.event.comment.body == '/breaking-change'
+        uses: actions/github-script@ed597411d8f924073f98dfc5c65a23a2325f34cd # v8.0.0
+        with:
+          script: |
+            // Add the breaking change label
+            await github.rest.issues.addLabels({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              issue_number: context.issue.number,
+              labels: ['breaking change']
+            });
+
+            // React to the comment to show it was processed
+            await github.rest.reactions.createForIssueComment({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              comment_id: context.payload.comment.id,
+              content: '+1'
+            });
+
+            // Add a reply comment to confirm the action
+            await github.rest.issues.createComment({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              issue_number: context.issue.number,
+              body: '✅ Added `breaking change` label to this PR.'
+            });
+
+      - name: Add deprecation label
+        if: github.event.comment.body == '/deprecation'
+        uses: actions/github-script@ed597411d8f924073f98dfc5c65a23a2325f34cd # v8.0.0
+        with:
+          script: |
+            // Add the deprecation label
+            await github.rest.issues.addLabels({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              issue_number: context.issue.number,
+              labels: ['deprecation']
+            });
+
+            // React to the comment to show it was processed
+            await github.rest.reactions.createForIssueComment({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              comment_id: context.payload.comment.id,
+              content: '+1'
+            });
+
+            // Add a reply comment to confirm the action
+            await github.rest.issues.createComment({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              issue_number: context.issue.number,
+              body: '✅ Added `deprecation` label to this PR.'
+            });
+
+      - name: Remove breaking change label
+        if: github.event.comment.body == '/remove-breaking-change'
+        uses: actions/github-script@ed597411d8f924073f98dfc5c65a23a2325f34cd # v8.0.0
+        with:
+          script: |
+            try {
+              // Remove the breaking change label
+              await github.rest.issues.removeLabel({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                issue_number: context.issue.number,
+                name: 'breaking change'
+              });
+
+              // React to the comment to show it was processed
+              await github.rest.reactions.createForIssueComment({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                comment_id: context.payload.comment.id,
+                content: '+1'
+              });
+
+              // Add a reply comment to confirm the action
+              await github.rest.issues.createComment({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                issue_number: context.issue.number,
+                body: '✅ Removed `breaking change` label from this PR.'
+              });
+            } catch (error) {
+              if (error.status === 404) {
+                // Label doesn't exist on the PR
+                await github.rest.reactions.createForIssueComment({
+                  owner: context.repo.owner,
+                  repo: context.repo.repo,
+                  comment_id: context.payload.comment.id,
+                  content: 'confused'
+                });
+
+                await github.rest.issues.createComment({
+                  owner: context.repo.owner,
+                  repo: context.repo.repo,
+                  issue_number: context.issue.number,
+                  body: '⚠️ The `breaking change` label was not found on this PR.'
+                });
+              } else {
+                throw error;
+              }
+            }
+
+      - name: Remove deprecation label
+        if: github.event.comment.body == '/remove-deprecation'
+        uses: actions/github-script@ed597411d8f924073f98dfc5c65a23a2325f34cd # v8.0.0
+        with:
+          script: |
+            try {
+              // Remove the deprecation label
+              await github.rest.issues.removeLabel({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                issue_number: context.issue.number,
+                name: 'deprecation'
+              });
+
+              // React to the comment to show it was processed
+              await github.rest.reactions.createForIssueComment({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                comment_id: context.payload.comment.id,
+                content: '+1'
+              });
+
+              // Add a reply comment to confirm the action
+              await github.rest.issues.createComment({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                issue_number: context.issue.number,
+                body: '✅ Removed `deprecation` label from this PR.'
+              });
+            } catch (error) {
+              if (error.status === 404) {
+                // Label doesn't exist on the PR
+                await github.rest.reactions.createForIssueComment({
+                  owner: context.repo.owner,
+                  repo: context.repo.repo,
+                  comment_id: context.payload.comment.id,
+                  content: 'confused'
+                });
+
+                await github.rest.issues.createComment({
+                  owner: context.repo.owner,
+                  repo: context.repo.repo,
+                  issue_number: context.issue.number,
+                  body: '⚠️ The `deprecation` label was not found on this PR.'
+                });
+              } else {
+                throw error;
+              }
+            }
\ No newline at end of file
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index 6b83f119410f..426871ca98bf 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -153,10 +153,8 @@ jobs:
           sed -n "0,/^## Version $VERSION /d;/^## Version /q;p" CHANGELOG.md \
             > /tmp/CHANGELOG_SECTION.md
 
-          # the complex perl regex is needed because markdown docs render newlines as soft wraps
-          # while release notes render them as line breaks
-          perl -0pe 's/(?<!\n)\n *(?!\n)(?![-*] )(?![1-9]+\. )/ /g' /tmp/CHANGELOG_SECTION.md \
-            >> /tmp/release-notes.txt
+          # Format changelog section for release notes (includes breaking changes handling)
+          .github/scripts/format-release-notes.sh /tmp/CHANGELOG_SECTION.md /tmp/release-notes.txt
 
           # conditional block not indented because of the heredoc
           if [[ $VERSION == *.0 ]]; then
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index da2e38058d2d..5f5936d92258 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -6,6 +6,39 @@ Before submitting new features or changes to current functionality, it is recomm
 [open an issue](https://github.com/open-telemetry/opentelemetry-java-instrumentation/issues/new)
 and discuss your ideas or propose the changes you wish to make.
 
+
+## Breaking Changes
+
+When your PR introduces a breaking change:
+
+* Add the `breaking change` label to your PR
+  - If you can't add labels directly, post a comment containing only `/breaking-change` and the label will be added automatically
+  - To remove the label, post a comment containing only `/remove-breaking-change`
+* Provide migration notes in the PR description:
+  - What is changing and why
+  - How users should update their code/configuration
+  - Code examples showing before/after usage (if applicable)
+
+**When to Use:**
+
+* API changes that break backward compatibility
+* Configuration changes that require user action
+* Behavioral changes that might affect existing users
+* Removal of deprecated features
+
+## Deprecations
+
+When your PR deprecates functionality:
+
+* Add the `deprecation` label to your PR
+  - If you can't add labels directly, post a comment containing only `/deprecation` and the label will be added automatically
+  - To remove the label, post a comment containing only `/remove-deprecation`
+* Provide deprecation details in the PR description:
+  - What is being deprecated and why
+  - What should be used instead (if applicable)
+  - Timeline for removal (if known)
+  - Any migration guidance
+
 ## Building
 
 This project requires Java 21 to build and run tests. Newer JDK's may work, but this version is used in CI.
diff --git a/RELEASING.md b/RELEASING.md
index ea6d6186705f..0cc432ae481b 100644
--- a/RELEASING.md
+++ b/RELEASING.md
@@ -29,6 +29,8 @@ the second Monday of the month (roughly a few days after the monthly minor relea
 - Merge a pull request to `main` updating the `CHANGELOG.md`.
   - The heading for the unreleased entries should be `## Unreleased`.
   - Use `.github/scripts/draft-change-log-entries.sh` as a starting point for writing the change log.
+  - The script will automatically include a "Breaking Changes" section for PRs labeled with `breaking change`.
+  - The script will automatically include a "Deprecations" section for PRs labeled with `deprecation`.
 - Run the [Prepare release branch workflow](https://github.com/open-telemetry/opentelemetry-java-instrumentation/actions/workflows/prepare-release-branch.yml).
   - Press the "Run workflow" button, and leave the default branch `main` selected.
   - Review and merge the two pull requests that it creates