diff --git a/Makefile b/Makefile
index 9caae554c..0f9791d03 100644
--- a/Makefile
+++ b/Makefile
@@ -225,3 +225,29 @@ serve-docs:
 	-it -p 4000:4000 \
 	jekyll/jekyll \
 	jekyll serve --livereload
+
+# gen-docs generates a new versioned docs directory under site/docs. It follows
+# the following process:
+#   1. Copies the contents of the most recently tagged docs directory into the new
+#      directory, to establish a useful baseline to diff against.
+#   2. Adds all copied content from step 1 to git's staging area via 'git add'.
+#   3. Replaces the contents of the new docs directory with the contents of the
+#      'master' docs directory, updating any version-specific links (e.g. to a
+#      specific branch of the GitHub repository) to use the new version
+#   4. Copies the previous version's ToC file and runs 'git add' to establish
+#      a useful baseline to diff against.
+#   5. Replaces the content of the new ToC file with the master ToC.
+#   6. Update site/_config.yml and site/_data/toc-mapping.yml to include entries
+#      for the new version.
+#
+# The unstaged changes in the working directory can now easily be diff'ed against the
+# staged changes using 'git diff' to review all docs changes made since the previous 
+# tagged version. Once the unstaged changes are ready, they can be added to the
+# staging area using 'git add' and then committed.
+#
+# To run gen-docs: "NEW_DOCS_VERSION=v1.1.0 make gen-docs"
+#
+# **NOTE**: there are additional manual steps required to finalize the process of generating
+# a new versioned docs site. The full process is documented in site/README-JEKYLL.md.
+gen-docs:
+	@hack/gen-docs.sh
diff --git a/hack/gen-docs.sh b/hack/gen-docs.sh
new file mode 100755
index 000000000..465096149
--- /dev/null
+++ b/hack/gen-docs.sh
@@ -0,0 +1,108 @@
+#!/bin/bash
+
+# Copyright 2019 the Velero contributors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+# gen-docs.sh is used for the "make gen-docs" target. See additional
+# documentation in the Makefile.
+
+set -o errexit
+set -o nounset
+set -o pipefail
+
+# don't run if there's already a directory for the target docs version
+if [[ -d site/docs/$NEW_DOCS_VERSION ]]; then
+    echo "ERROR: site/docs/$NEW_DOCS_VERSION already exists"
+    exit 1
+fi
+
+# get the alphabetically last item in site/docs to use as PREVIOUS_DOCS_VERSION
+# if not explicitly specified by the user
+if [[ -z "${PREVIOUS_DOCS_VERSION:-}" ]]; then
+    echo "PREVIOUS_DOCS_VERSION was not specified, getting the latest version"
+    PREVIOUS_DOCS_VERSION=$(ls -1 site/docs/ | tail -n 1)
+fi
+
+# make a copy of the previous versioned docs dir
+echo "Creating copy of docs directory site/docs/$PREVIOUS_DOCS_VERSION in site/docs/$NEW_DOCS_VERSION"
+cp -r site/docs/${PREVIOUS_DOCS_VERSION}/ site/docs/${NEW_DOCS_VERSION}/
+
+# 'git add' the previous version's docs as-is so we get a useful diff when we copy the master docs in
+echo "Running 'git add' for previous version's doc contents to use as a base for diff"
+git add site/docs/${NEW_DOCS_VERSION}
+
+# now copy the contents of site/docs/master into the same directory so we can get a nice
+# git diff of what changed since previous version
+echo "Copying site/docs/master/ to site/docs/${NEW_DOCS_VERSION}/"
+rm -rf site/docs/${NEW_DOCS_VERSION}/ && cp -r site/docs/master/ site/docs/${NEW_DOCS_VERSION}/
+
+# make a copy of the previous versioned ToC
+NEW_DOCS_TOC="$(echo ${NEW_DOCS_VERSION} | tr . -)-toc"
+PREVIOUS_DOCS_TOC="$(echo ${PREVIOUS_DOCS_VERSION} | tr . -)-toc"
+
+echo "Creating copy of site/_data/$PREVIOUS_DOCS_TOC.yml at site/_data/$NEW_DOCS_TOC.yml"
+cp site/_data/$PREVIOUS_DOCS_TOC.yml site/_data/$NEW_DOCS_TOC.yml
+
+# 'git add' the previous version's ToC content as-is so we get a useful diff when we copy the master ToC in
+echo "Running 'git add' for previous version's ToC to use as a base for diff"
+git add site/_data/$NEW_DOCS_TOC.yml
+
+# now copy the master ToC so we can get a nice git diff of what changed since previous version
+echo "Copying site/_data/master-toc.yml to site/_data/$NEW_DOCS_TOC.yml"
+rm site/_data/$NEW_DOCS_TOC.yml && cp site/_data/master-toc.yml site/_data/$NEW_DOCS_TOC.yml
+
+# replace known version-specific links -- the sed syntax is slightly different in OS X and Linux,
+# so check which OS we're running on.
+if [[ $(uname) == "Darwin" ]]; then
+    echo "[OS X] updating version-specific links"
+    find site/docs/${NEW_DOCS_VERSION} -type f -name "*.md" | xargs sed -i '' "s|https://velero.io/docs/master|https://velero.io/docs/$NEW_DOCS_VERSION|g"
+    find site/docs/${NEW_DOCS_VERSION} -type f -name "*.md" | xargs sed -i '' "s|https://github.com/heptio/velero/blob/master|https://github.com/heptio/velero/blob/$NEW_DOCS_VERSION|g"
+
+    echo "[OS X] Updating latest version in _config.yml"
+    sed -i '' "s/latest: ${PREVIOUS_DOCS_VERSION}/latest: ${NEW_DOCS_VERSION}/" site/_config.yml
+
+    # newlines and lack of indentation are requirements for this sed syntax
+    # which is doing an append
+    echo "[OS X] Adding latest version to versions list in _config.yml"
+    sed -i '' "/- master/a\\
+- ${NEW_DOCS_VERSION}
+" site/_config.yml
+
+    echo "[OS X] Adding ToC mapping entry"
+    sed -i '' "/master: master-toc/a\\
+${NEW_DOCS_VERSION}: ${NEW_DOCS_TOC}
+" site/_data/toc-mapping.yml
+
+else
+    echo "[Linux] updating version-specific links"
+    find site/docs/${NEW_DOCS_VERSION} -type f -name "*.md" | xargs sed -i'' "s|https://velero.io/docs/master|https://velero.io/docs/$NEW_DOCS_VERSION|g"
+    find site/docs/${NEW_DOCS_VERSION} -type f -name "*.md" | xargs sed -i'' "s|https://github.com/heptio/velero/blob/master|https://github.com/heptio/velero/blob/$NEW_DOCS_VERSION|g"
+
+    echo "[Linux] Updating latest version in _config.yml"
+    sed -i'' "s/latest: ${PREVIOUS_DOCS_VERSION}/latest: ${NEW_DOCS_VERSION}/" site/_config.yml
+    
+    echo "[Linux] Adding latest version to versions list in _config.yml"
+    sed -i'' "/- master/a - ${NEW_DOCS_VERSION}" site/_config.yml
+    
+    echo "[Linux] Adding ToC mapping entry"
+    sed -i'' "/master: master-toc/a ${NEW_DOCS_VERSION}: ${NEW_DOCS_TOC}" site/_data/toc-mapping.yml
+fi
+
+echo "Success! site/docs/$NEW_DOCS_VERSION has been created."
+echo ""
+echo "The next steps are:"
+echo "  1. Consult site/README-JEKYLL.md for further manual steps required to finalize the new versioned docs generation."
+echo "  2. Run a 'git diff' to review all changes made to the docs since the previous version."
+echo "  3. Make any manual changes/corrections necessary."
+echo "  4. Run 'git add' to stage all unstaged changes, then 'git commit'."
diff --git a/site/README-JEKYLL.md b/site/README-JEKYLL.md
index 5ed0b28a6..ceba8b142 100644
--- a/site/README-JEKYLL.md
+++ b/site/README-JEKYLL.md
@@ -31,3 +31,17 @@ This mirrors the plug-ins used by GitHub Pages on your local machine including J
 7. View your website at http://127.0.0.1:4000/
 8. Commit any changes and push everything to your fork.
 9. Once you're ready, submit a PR of your changes. Netlify will automatically generate a preview of your changes.
+
+
+# Adding a New Docs Version
+
+To add a new set of versioned docs to go with a new Velero release:
+
+1. In the root of the repository, run:
+
+   ```bash
+   # set to the appropriate version number
+   NEW_DOCS_VERSION=vX.Y.Z make gen-docs
+   ```
+
+1. In `site/_config.yml`, under the `defaults` field, add an entry for the new version just under `master` by copying the most recent version's entry and updating the version numbers.
diff --git a/site/_data/master-toc.yml b/site/_data/master-toc.yml
index 88c632ec4..eea1bbf49 100644
--- a/site/_data/master-toc.yml
+++ b/site/_data/master-toc.yml
@@ -1,7 +1,3 @@
-# historically we haven't provided a new TOC for the master branch docs
-# but a doc reorg suggests that it would be useful at this point
-# for future docs builds: use this file as the basis for new version TOCs
-
 toc:
   - title: Introduction
     subfolderitems:
diff --git a/site/_data/toc-mapping.yml b/site/_data/toc-mapping.yml
index ab2dffcdc..7c0958a15 100644
--- a/site/_data/toc-mapping.yml
+++ b/site/_data/toc-mapping.yml
@@ -3,7 +3,7 @@
 # that the navigation for older versions still work.
 
 master: master-toc
-v1.0.0: v1-0-toc
+v1.0.0: v1-0-0-toc
 v0.11.0: v011-toc
 v0.10.0: v010-toc
 v0.9.0: v9-toc
diff --git a/site/_data/v1-0-toc.yml b/site/_data/v1-0-0-toc.yml
similarity index 100%
rename from site/_data/v1-0-toc.yml
rename to site/_data/v1-0-0-toc.yml