diff --git a/.github/workflows/docs-preview.yaml b/.github/workflows/docs-preview.yaml
index 12e619c27c..c585a61acd 100644
--- a/.github/workflows/docs-preview.yaml
+++ b/.github/workflows/docs-preview.yaml
@@ -2,8 +2,13 @@
 # pull request that touches files under docs/ is opened.  The preview
 # is served by coder.com's branch-preview feature at /docs/@<branch>.
 #
+# The link deep-links to the first added/modified/renamed Markdown file
+# under docs/ so reviewers land on the page that actually changed.
 # Branch names are URL-encoded so that names containing slashes or
 # other special characters produce working links.
+#
+# If the PR only deletes Markdown files (or only changes non-Markdown
+# files such as images or manifest.json), no comment is posted.
 
 name: docs-preview
 
@@ -30,14 +35,71 @@ jobs:
           PR_NUMBER: ${{ github.event.pull_request.number }}
           REPO: ${{ github.repository }}
         run: |
+          # Fetch the list of non-deleted files from the PR.  This is
+          # intentionally not piped into grep so that a gh-api failure
+          # (network, auth, rate-limit) propagates immediately instead
+          # of being swallowed by `|| true`.
+          all_files=$(gh api --paginate \
+            "repos/${REPO}/pulls/${PR_NUMBER}/files" \
+            --jq '.[] | select(.status != "removed") | .filename')
+
+          # Pick the first Markdown file under docs/.  `|| true` keeps
+          # the pipeline from failing when grep finds no matches or
+          # head triggers SIGPIPE under `set -o pipefail`.
+          first_doc=$(printf '%s\n' "$all_files" \
+            | grep -E '^docs/.*\.md$' \
+            | head -n 1) || true
+
+          if [ -z "$first_doc" ]; then
+            echo "No added/modified Markdown files under docs/, skipping preview comment."
+            exit 0
+          fi
+
+          # Map the repo path to the docs site URL path.
+          #   docs/README.md           -> ""           (docs root)
+          #   docs/<dir>/index.md      -> "<dir>"      (directory index)
+          #   docs/<dir>/README.md     -> "<dir>"      (directory index)
+          #   docs/<dir>/<file>.md     -> "<dir>/<file>"
+          rel="${first_doc#docs/}"
+          case "$rel" in
+            README.md)
+              page_path=""
+              ;;
+            *)
+              base="$(basename "$rel")"
+              dir="$(dirname "$rel")"
+              if [ "$dir" = "." ]; then
+                dir=""
+              fi
+              case "$base" in
+                index.md|README.md)
+                  page_path="$dir"
+                  ;;
+                *)
+                  stripped="${base%.md}"
+                  if [ -z "$dir" ]; then
+                    page_path="$stripped"
+                  else
+                    page_path="${dir}/${stripped}"
+                  fi
+                  ;;
+              esac
+              ;;
+          esac
+
           # URL-encode the branch name so slashes and special
-          # characters don't break the preview URL.
-          encoded=$(jq -rn --arg b "$BRANCH" '$b | @uri')
-          url="https://coder.com/docs/@${encoded}"
+          # characters don't break the preview URL.  The page path is
+          # left as-is because its components are simple ASCII path
+          # segments and the slashes between them must be preserved.
+          encoded_branch=$(jq -rn --arg b "$BRANCH" '$b | @uri')
+          url="https://coder.com/docs/@${encoded_branch}"
+          if [ -n "$page_path" ]; then
+            url="${url}/${page_path}"
+          fi
 
           gh pr comment "${PR_NUMBER}" \
             --repo "${REPO}" \
             --body "## Docs preview
-          [:book: View docs preview](${url})
+          [:book: View docs preview](${url}) for \`${first_doc}\`
 
           <!-- docs-preview -->"
diff --git a/.github/workflows/test-docs-preview-mapper.sh b/.github/workflows/test-docs-preview-mapper.sh
new file mode 100755
index 0000000000..6ebf9e7473
--- /dev/null
+++ b/.github/workflows/test-docs-preview-mapper.sh
@@ -0,0 +1,89 @@
+#!/bin/bash
+# Regression tests for the path-mapping logic in docs-preview.yaml.
+# The mapper converts a repo-relative docs path into the URL path
+# used by the docs site preview. Five distinct branches exist in the
+# case block; every branch must be covered here.
+
+set -euo pipefail
+
+# map_doc_path replicates the case block from docs-preview.yaml so
+# we can exercise it without running the full workflow.
+map_doc_path() {
+	local first_doc="$1"
+	local rel="${first_doc#docs/}"
+	local page_path
+
+	case "$rel" in
+	README.md)
+		page_path=""
+		;;
+	*)
+		local base dir stripped
+		base="$(basename "$rel")"
+		dir="$(dirname "$rel")"
+		if [ "$dir" = "." ]; then
+			dir=""
+		fi
+		case "$base" in
+		index.md | README.md)
+			page_path="$dir"
+			;;
+		*)
+			stripped="${base%.md}"
+			if [ -z "$dir" ]; then
+				page_path="$stripped"
+			else
+				page_path="${dir}/${stripped}"
+			fi
+			;;
+		esac
+		;;
+	esac
+
+	printf '%s' "$page_path"
+}
+
+failures=0
+
+assert_maps_to() {
+	local input="$1"
+	local expected="$2"
+	local actual
+	actual="$(map_doc_path "$input")"
+	if [ "$actual" = "$expected" ]; then
+		echo "PASS: $input -> \"$expected\""
+	else
+		echo "FAIL: $input -> \"$actual\" (expected \"$expected\")"
+		failures=$((failures + 1))
+	fi
+}
+
+# Branch 1: top-level README maps to the docs root.
+assert_maps_to "docs/README.md" ""
+
+# Branch 2: nested index.md strips the filename, leaving the dir.
+assert_maps_to "docs/install/index.md" "install"
+
+# Branch 3: nested README.md behaves the same as index.md.
+assert_maps_to "docs/admin/README.md" "admin"
+
+# Branch 4: nested regular file strips .md and keeps the dir prefix.
+assert_maps_to "docs/ai-coder/tasks.md" "ai-coder/tasks"
+
+# Branch 5: top-level non-README file strips .md with no dir prefix.
+assert_maps_to "docs/CHANGELOG.md" "CHANGELOG"
+
+# Additional coverage for edge cases and deeper nesting.
+assert_maps_to "docs/index.md" ""
+assert_maps_to "docs/about/contributing/CONTRIBUTING.md" "about/contributing/CONTRIBUTING"
+assert_maps_to "docs/admin/groups.md" "admin/groups"
+assert_maps_to "docs/tutorials/best-practices/index.md" "tutorials/best-practices"
+
+if [ "$failures" -gt 0 ]; then
+	echo ""
+	echo "$failures test(s) failed."
+	exit 1
+fi
+
+echo ""
+echo "All tests passed."