diff --git a/src/api-umbrella/proxy/middleware/api_matcher.lua b/src/api-umbrella/proxy/middleware/api_matcher.lua
index 2a001c53c..623efccef 100644
--- a/src/api-umbrella/proxy/middleware/api_matcher.lua
+++ b/src/api-umbrella/proxy/middleware/api_matcher.lua
@@ -3,7 +3,6 @@ local stringx = require "pl.stringx"
 local utils = require "api-umbrella.proxy.utils"
 
 local append_array = utils.append_array
-local gsub = string.gsub
 local set_uri = utils.set_uri
 local startswith = stringx.startswith
 
@@ -50,8 +49,10 @@ return function(active_config)
 
   if api and url_match then
     -- Rewrite the URL prefix path.
-    local new_path = gsub(request_path, url_match["_frontend_prefix_matcher"], url_match["backend_prefix"], 1)
-    if new_path ~= request_path then
+    local new_path, _, new_path_err = ngx.re.sub(request_path, url_match["_frontend_prefix_regex"], url_match["backend_prefix"], "jo")
+    if new_path_err then
+      ngx.log(ngx.ERR, "regex error: ", new_path_err)
+    elseif new_path ~= request_path then
       set_uri(new_path)
     end
 
diff --git a/src/api-umbrella/proxy/middleware/rewrite_response.lua b/src/api-umbrella/proxy/middleware/rewrite_response.lua
index d615214a7..2dfd8e3b9 100644
--- a/src/api-umbrella/proxy/middleware/rewrite_response.lua
+++ b/src/api-umbrella/proxy/middleware/rewrite_response.lua
@@ -3,7 +3,6 @@ local url = require "socket.url"
 local utils = require "api-umbrella.proxy.utils"
 
 local append_args = utils.append_args
-local gsub = string.gsub
 local startswith = stringx.startswith
 local url_build = url.build
 local url_parse = url.parse
@@ -126,14 +125,30 @@ local function rewrite_redirects()
     changed = true
   end
 
-  if host_matches or relative then
-    if matched_api and matched_api["url_matches"] then
-      for _, url_match in ipairs(matched_api["url_matches"]) do
-        if startswith(parsed["path"], url_match["backend_prefix"]) then
-          parsed["path"] = gsub(parsed["path"], url_match["_backend_prefix_matcher"], url_match["frontend_prefix"], 1)
-          changed = true
-          break
-        end
+  -- If the redirect being returned possibly contains paths for the underlying
+  -- backend URL, then rewrite the path.
+  if (host_matches or relative) and matched_api then
+    -- If the redirect path begins with the backend prefix, then consider it
+    -- for rewriting.
+    local url_match = ngx.ctx.matched_api_url_match
+    if url_match and startswith(parsed["path"], url_match["backend_prefix"]) then
+      -- As long as the patah matches the backend prefix, mark as changed, so
+      -- the api key is appended (regardless of whether we actually replaced
+      -- the path).
+      changed = true
+
+      -- Don't rewrite the path if the frontend prefix contains the backend
+      -- prefix and the redirect path already contains the frontend prefix.
+      --
+      -- This helps ensure that if the API backend is already returning
+      -- public/frontend URLs, we don't try to rewrite these again. -
+      local rewrite_path = true
+      if url_match["_frontend_prefix_contains_backend_prefix"] and startswith(parsed["path"], url_match["frontend_prefix"]) then
+        rewrite_path = false
+      end
+
+      if rewrite_path then
+        parsed["path"] = ngx.re.sub(parsed["path"], url_match["_backend_prefix_regex"], url_match["frontend_prefix"], "jo")
       end
     end
   end
diff --git a/src/api-umbrella/proxy/models/active_config.lua b/src/api-umbrella/proxy/models/active_config.lua
index e0780c1f8..b4c0baa98 100644
--- a/src/api-umbrella/proxy/models/active_config.lua
+++ b/src/api-umbrella/proxy/models/active_config.lua
@@ -9,11 +9,11 @@ local random_token = require "api-umbrella.utils.random_token"
 local resolve_backend_dns = require "api-umbrella.proxy.jobs.resolve_backend_dns"
 local tablex = require "pl.tablex"
 local utils = require "api-umbrella.proxy.utils"
+local startswith = require("pl.stringx").startswith
 
 local append_array = utils.append_array
 local cache_computed_settings = utils.cache_computed_settings
 local deepcopy = tablex.deepcopy
-local escape = plutils.escape
 local set_packed = utils.set_packed
 local size = tablex.size
 local split = plutils.split
@@ -55,8 +55,18 @@ local function cache_computed_api(api)
 
   if api["url_matches"] then
     for _, url_match in ipairs(api["url_matches"]) do
-      url_match["_frontend_prefix_matcher"] = "^" .. escape(url_match["frontend_prefix"])
-      url_match["_backend_prefix_matcher"] = "^" .. escape(url_match["backend_prefix"])
+      url_match["_frontend_prefix_regex"] = "^" .. escape_regex(url_match["frontend_prefix"])
+      url_match["_backend_prefix_regex"] = "^" .. escape_regex(url_match["backend_prefix"])
+
+      url_match["_frontend_prefix_contains_backend_prefix"] = false
+      if startswith(url_match["frontend_prefix"], url_match["backend_prefix"]) then
+        url_match["_frontend_prefix_contains_backend_prefix"] = true
+      end
+
+      url_match["_backend_prefix_contains_frontend_prefix"] = false
+      if startswith(url_match["backend_prefix"], url_match["frontend_prefix"]) then
+        url_match["_backend_prefix_contains_frontend_prefix"] = true
+      end
     end
   end
 
diff --git a/templates/etc/test-env/nginx/apis.conf.mustache b/templates/etc/test-env/nginx/apis.conf.mustache
index 156ac69ec..2ba18dc7c 100644
--- a/templates/etc/test-env/nginx/apis.conf.mustache
+++ b/templates/etc/test-env/nginx/apis.conf.mustache
@@ -92,7 +92,7 @@ server {
     echo -n "Hello World";
   }
 
-  location = /redirect {
+  location /redirect {
     rewrite_by_lua_block {
       ngx.redirect(ngx.unescape_uri(ngx.var.arg_to or "/hello"))
     }
diff --git a/test/proxy/response_rewriting/test_redirects.rb b/test/proxy/response_rewriting/test_redirects.rb
index 54e8159df..7538c1caf 100644
--- a/test/proxy/response_rewriting/test_redirects.rb
+++ b/test/proxy/response_rewriting/test_redirects.rb
@@ -10,82 +10,295 @@ def setup
     once_per_class_setup do
       prepend_api_backends([
         {
-          :frontend_host => "frontend.foo",
+          :frontend_host => unique_test_class_hostname,
           :backend_host => "example.com",
           :servers => [{ :host => "127.0.0.1", :port => 9444 }],
-          :url_matches => [{ :frontend_prefix => "/#{unique_test_class_id}/front/end/path", :backend_prefix => "/backend-prefix" }],
+          :url_matches => [
+            {
+              # Add url matches that match the backend (since / will match
+              # everything), but don't match the frontend prefix, to ensure
+              # these don't get used during rewriting.
+              :frontend_prefix => "/unused-matcher-with-root-backend-prefix",
+              :backend_prefix => "/",
+            },
+            {
+              :frontend_prefix => "/frontend-prefix-routes-to-path",
+              :backend_prefix => "/backend-prefix",
+            },
+            {
+              :frontend_prefix => "/frontend-prefix-routes-to-root/",
+              :backend_prefix => "/",
+            },
+            {
+              :frontend_prefix => "/redirect/frontend-prefix-contains-backend-prefix/frontend-piece/",
+              :backend_prefix => "/redirect/frontend-prefix-contains-backend-prefix/",
+            },
+            {
+              :frontend_prefix => "/redirect/backend-prefix-contains-frontend-prefix/",
+              :backend_prefix => "/redirect/backend-prefix-contains-frontend-prefix/backend-piece/",
+            },
+            {
+              :frontend_prefix => "/backend-prefix/redirect",
+              :backend_prefix => "/backend-prefix/redirect",
+            },
+            {
+              :frontend_prefix => "/",
+              :backend_prefix => "/backend-prefix/",
+            },
+            {
+              :frontend_prefix => "/unused-matcher-with-root-backend-prefix-last",
+              :backend_prefix => "/",
+            },
+          ],
         },
       ])
     end
   end
 
-  def test_relative_leaves_unknown_path
-    response = make_redirect_request("/somewhere")
-    assert_equal("/somewhere", response.headers["location"])
+  def test_relative_unknown_path
+    assert_redirects("/somewhere", {
+      :frontend_prefix_routes_to_path => "/somewhere",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/somewhere?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/somewhere",
+      :frontend_prefix_equals_backend_prefix => "/somewhere",
+      :frontend_prefix_contains_backend_prefix => "/somewhere",
+      :backend_prefix_contains_frontend_prefix => "/somewhere",
+    })
   end
 
-  def test_relative_rewrites_frontend_prefix
-    response = make_redirect_request("/backend-prefix/more/here")
-    assert_equal("/#{unique_test_class_id}/front/end/path/more/here?api_key=#{api_key}", response.headers["location"])
+  def test_relative_frontend_prefix_routes_to_root
+    assert_redirects("/frontend-prefix-routes-to-root/foo", {
+      :frontend_prefix_routes_to_path => "/frontend-prefix-routes-to-root/foo",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/foo?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/frontend-prefix-routes-to-root/foo",
+      :frontend_prefix_equals_backend_prefix => "/frontend-prefix-routes-to-root/foo",
+      :frontend_prefix_contains_backend_prefix => "/frontend-prefix-routes-to-root/foo",
+      :backend_prefix_contains_frontend_prefix => "/frontend-prefix-routes-to-root/foo",
+    })
   end
 
-  def test_absolute_leaves_unknown_domain
-    response = make_redirect_request("http://other_url.com/hello")
-    assert_equal("http://other_url.com/hello", response.headers["location"])
+  def test_relative_frontend_prefix_routes_to_root_incomplete_path
+    assert_redirects("/frontend-prefix-routes-to-roo", {
+      :frontend_prefix_routes_to_path => "/frontend-prefix-routes-to-roo",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/frontend-prefix-routes-to-roo?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/frontend-prefix-routes-to-roo",
+      :frontend_prefix_equals_backend_prefix => "/frontend-prefix-routes-to-roo",
+      :frontend_prefix_contains_backend_prefix => "/frontend-prefix-routes-to-roo",
+      :backend_prefix_contains_frontend_prefix => "/frontend-prefix-routes-to-roo",
+    })
   end
 
-  def test_absolute_rewrites_backend_domain
-    response = make_redirect_request("http://example.com/hello")
-    assert_equal("http://frontend.foo:9080/hello?api_key=#{api_key}", response.headers["location"])
+  def test_relative_frontend_prefix_routes_to_path
+    assert_redirects("/frontend-prefix-routes-to-path", {
+      :frontend_prefix_routes_to_path => "/frontend-prefix-routes-to-path",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/frontend-prefix-routes-to-path?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/frontend-prefix-routes-to-path",
+      :frontend_prefix_equals_backend_prefix => "/frontend-prefix-routes-to-path",
+      :frontend_prefix_contains_backend_prefix => "/frontend-prefix-routes-to-path",
+      :backend_prefix_contains_frontend_prefix => "/frontend-prefix-routes-to-path",
+    })
   end
 
-  def test_absolute_rewrites_backend_domain_https
-    response = make_redirect_request("https://example.com/hello")
-    assert_equal("https://frontend.foo:9081/hello?api_key=#{api_key}", response.headers["location"])
+  def test_relative_frontend_prefix_contains_backend_prefix_partial
+    assert_redirects("/redirect/frontend-prefix-contains-backend-prefix/", {
+      :frontend_prefix_routes_to_path => "/redirect/frontend-prefix-contains-backend-prefix/",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/redirect/frontend-prefix-contains-backend-prefix/?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/redirect/frontend-prefix-contains-backend-prefix/",
+      :frontend_prefix_equals_backend_prefix => "/redirect/frontend-prefix-contains-backend-prefix/",
+      :frontend_prefix_contains_backend_prefix => "/redirect/frontend-prefix-contains-backend-prefix/frontend-piece/?api_key=#{api_key}",
+      :backend_prefix_contains_frontend_prefix => "/redirect/frontend-prefix-contains-backend-prefix/",
+    })
+  end
+
+  def test_relative_frontend_prefix_contains_backend_prefix_complete
+    assert_redirects("/redirect/frontend-prefix-contains-backend-prefix/frontend-piece/", {
+      :frontend_prefix_routes_to_path => "/redirect/frontend-prefix-contains-backend-prefix/frontend-piece/",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/redirect/frontend-prefix-contains-backend-prefix/frontend-piece/?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/redirect/frontend-prefix-contains-backend-prefix/frontend-piece/",
+      :frontend_prefix_equals_backend_prefix => "/redirect/frontend-prefix-contains-backend-prefix/frontend-piece/",
+      :frontend_prefix_contains_backend_prefix => "/redirect/frontend-prefix-contains-backend-prefix/frontend-piece/?api_key=#{api_key}",
+      :backend_prefix_contains_frontend_prefix => "/redirect/frontend-prefix-contains-backend-prefix/frontend-piece/",
+    })
+  end
+
+  def test_relative_backend_prefix_contains_frontend_prefix_partial
+    assert_redirects("/redirect/backend-prefix-contains-frontend-prefix/", {
+      :frontend_prefix_routes_to_path => "/redirect/backend-prefix-contains-frontend-prefix/",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/redirect/backend-prefix-contains-frontend-prefix/?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/redirect/backend-prefix-contains-frontend-prefix/",
+      :frontend_prefix_equals_backend_prefix => "/redirect/backend-prefix-contains-frontend-prefix/",
+      :frontend_prefix_contains_backend_prefix => "/redirect/backend-prefix-contains-frontend-prefix/",
+      :backend_prefix_contains_frontend_prefix => "/redirect/backend-prefix-contains-frontend-prefix/",
+    })
+  end
+
+  def test_relative_backend_prefix_contains_frontend_prefix_complete
+    assert_redirects("/redirect/backend-prefix-contains-frontend-prefix/backend-piece/", {
+      :frontend_prefix_routes_to_path => "/redirect/backend-prefix-contains-frontend-prefix/backend-piece/",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/redirect/backend-prefix-contains-frontend-prefix/backend-piece/?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/redirect/backend-prefix-contains-frontend-prefix/backend-piece/",
+      :frontend_prefix_equals_backend_prefix => "/redirect/backend-prefix-contains-frontend-prefix/backend-piece/",
+      :frontend_prefix_contains_backend_prefix => "/redirect/backend-prefix-contains-frontend-prefix/backend-piece/",
+      :backend_prefix_contains_frontend_prefix => "/redirect/backend-prefix-contains-frontend-prefix/?api_key=#{api_key}",
+    })
+  end
+
+  def test_relative_frontend_prefix_equals_backend_prefix
+    assert_redirects("/backend-prefix/more/here", {
+      :frontend_prefix_routes_to_path => "/frontend-prefix-routes-to-path/more/here?api_key=#{api_key}",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/backend-prefix/more/here?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/more/here?api_key=#{api_key}",
+      :frontend_prefix_equals_backend_prefix => "/backend-prefix/more/here",
+      :frontend_prefix_contains_backend_prefix => "/backend-prefix/more/here",
+      :backend_prefix_contains_frontend_prefix => "/backend-prefix/more/here",
+    })
+  end
+
+  def test_relative_frontend_prefix_equals_backend_prefix_incomplete
+    assert_redirects("/backend-prefi", {
+      :frontend_prefix_routes_to_path => "/backend-prefi",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/backend-prefi?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/backend-prefi",
+      :frontend_prefix_equals_backend_prefix => "/backend-prefi",
+      :frontend_prefix_contains_backend_prefix => "/backend-prefi",
+      :backend_prefix_contains_frontend_prefix => "/backend-prefi",
+    })
+  end
+
+  def test_absolute_unknown_host
+    assert_redirects("http://other_url.com/hello", {
+      :frontend_prefix_routes_to_path => "http://other_url.com/hello",
+      :frontend_prefix_routes_to_root => "http://other_url.com/hello",
+      :frontend_root_routes_to_path => "http://other_url.com/hello",
+      :frontend_prefix_equals_backend_prefix => "http://other_url.com/hello",
+      :frontend_prefix_contains_backend_prefix => "http://other_url.com/hello",
+      :backend_prefix_contains_frontend_prefix => "http://other_url.com/hello",
+    })
+  end
+
+  def test_absolute_matching_host
+    assert_redirects("http://example.com/hello", {
+      :frontend_prefix_routes_to_path => "http://#{unique_test_class_hostname}:9080/hello?api_key=#{api_key}",
+      :frontend_prefix_routes_to_root => "http://#{unique_test_class_hostname}:9080/frontend-prefix-routes-to-root/hello?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "http://#{unique_test_class_hostname}:9080/hello?api_key=#{api_key}",
+      :frontend_prefix_equals_backend_prefix => "http://#{unique_test_class_hostname}:9080/hello?api_key=#{api_key}",
+      :frontend_prefix_contains_backend_prefix => "http://#{unique_test_class_hostname}:9080/hello?api_key=#{api_key}",
+      :backend_prefix_contains_frontend_prefix => "http://#{unique_test_class_hostname}:9080/hello?api_key=#{api_key}",
+    })
+  end
+
+  def test_absolute_matching_host_https
+    assert_redirects("https://example.com/hello", {
+      :frontend_prefix_routes_to_path => "https://#{unique_test_class_hostname}:9081/hello?api_key=#{api_key}",
+      :frontend_prefix_routes_to_root => "https://#{unique_test_class_hostname}:9081/frontend-prefix-routes-to-root/hello?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "https://#{unique_test_class_hostname}:9081/hello?api_key=#{api_key}",
+      :frontend_prefix_equals_backend_prefix => "https://#{unique_test_class_hostname}:9081/hello?api_key=#{api_key}",
+      :frontend_prefix_contains_backend_prefix => "https://#{unique_test_class_hostname}:9081/hello?api_key=#{api_key}",
+      :backend_prefix_contains_frontend_prefix => "https://#{unique_test_class_hostname}:9081/hello?api_key=#{api_key}",
+    })
   end
 
   def test_absolute_requires_full_domain_match
-    response = make_redirect_request("http://eeexample.com/hello")
-    assert_equal("http://eeexample.com/hello", response.headers["location"])
+    assert_redirects("http://eeexample.com/hello", {
+      :frontend_prefix_routes_to_path => "http://eeexample.com/hello",
+      :frontend_prefix_routes_to_root => "http://eeexample.com/hello",
+      :frontend_root_routes_to_path => "http://eeexample.com/hello",
+      :frontend_prefix_equals_backend_prefix => "http://eeexample.com/hello",
+      :frontend_prefix_contains_backend_prefix => "http://eeexample.com/hello",
+      :backend_prefix_contains_frontend_prefix => "http://eeexample.com/hello",
+    })
   end
 
   def test_absolute_rewrites_frontend_prefix_path
-    response = make_redirect_request("http://example.com/backend-prefix/")
-    assert_equal("http://frontend.foo:9080/#{unique_test_class_id}/front/end/path/?api_key=#{api_key}", response.headers["location"])
+    assert_redirects("http://example.com/backend-prefix/", {
+      :frontend_prefix_routes_to_path => "http://#{unique_test_class_hostname}:9080/frontend-prefix-routes-to-path/?api_key=#{api_key}",
+      :frontend_prefix_routes_to_root => "http://#{unique_test_class_hostname}:9080/frontend-prefix-routes-to-root/backend-prefix/?api_key=#{api_key}",
+      :frontend_root_routes_to_path => "http://#{unique_test_class_hostname}:9080/?api_key=#{api_key}",
+      :frontend_prefix_equals_backend_prefix => "http://#{unique_test_class_hostname}:9080/backend-prefix/?api_key=#{api_key}",
+      :frontend_prefix_contains_backend_prefix => "http://#{unique_test_class_hostname}:9080/backend-prefix/?api_key=#{api_key}",
+      :backend_prefix_contains_frontend_prefix => "http://#{unique_test_class_hostname}:9080/backend-prefix/?api_key=#{api_key}",
+    })
   end
 
   def test_relative_unknown_path_leaves_query_params
-    response = make_redirect_request("/somewhere?param=example.com")
-    assert_equal("/somewhere?param=example.com", response.headers["location"])
+    assert_redirects("/somewhere?param=example.com", {
+      :frontend_prefix_routes_to_path => "/somewhere?param=example.com",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/somewhere?param=example.com&api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/somewhere?param=example.com",
+      :frontend_prefix_equals_backend_prefix => "/somewhere?param=example.com",
+      :frontend_prefix_contains_backend_prefix => "/somewhere?param=example.com",
+      :backend_prefix_contains_frontend_prefix => "/somewhere?param=example.com",
+    })
   end
 
   def test_relative_rewrite_keeps_query_params
-    response = make_redirect_request("/backend-prefix/more/here?some=param&and=another")
-    assert_equal("/#{unique_test_class_id}/front/end/path/more/here?some=param&and=another&api_key=#{api_key}", response.headers["location"])
+    assert_redirects("/backend-prefix/more/here?some=param&and=another", {
+      :frontend_prefix_routes_to_path => "/frontend-prefix-routes-to-path/more/here?some=param&and=another&api_key=#{api_key}",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/backend-prefix/more/here?some=param&and=another&api_key=#{api_key}",
+      :frontend_root_routes_to_path => "/more/here?some=param&and=another&api_key=#{api_key}",
+      :frontend_prefix_equals_backend_prefix => "/backend-prefix/more/here?some=param&and=another",
+      :frontend_prefix_contains_backend_prefix => "/backend-prefix/more/here?some=param&and=another",
+      :backend_prefix_contains_frontend_prefix => "/backend-prefix/more/here?some=param&and=another",
+    })
   end
 
   def test_absolute_rewrite_keeps_query_params
-    response = make_redirect_request("http://example.com/?some=param&and=another")
-    assert_equal("http://frontend.foo:9080/?some=param&and=another&api_key=#{api_key}", response.headers["location"])
+    assert_redirects("http://example.com/?some=param&and=another", {
+      :frontend_prefix_routes_to_path => "http://#{unique_test_class_hostname}:9080/?some=param&and=another&api_key=#{api_key}",
+      :frontend_prefix_routes_to_root => "http://#{unique_test_class_hostname}:9080/frontend-prefix-routes-to-root/?some=param&and=another&api_key=#{api_key}",
+      :frontend_root_routes_to_path => "http://#{unique_test_class_hostname}:9080/?some=param&and=another&api_key=#{api_key}",
+      :frontend_prefix_equals_backend_prefix => "http://#{unique_test_class_hostname}:9080/?some=param&and=another&api_key=#{api_key}",
+      :frontend_prefix_contains_backend_prefix => "http://#{unique_test_class_hostname}:9080/?some=param&and=another&api_key=#{api_key}",
+      :backend_prefix_contains_frontend_prefix => "http://#{unique_test_class_hostname}:9080/?some=param&and=another&api_key=#{api_key}",
+    })
   end
 
   def test_leaves_empty_redirect
-    response = make_redirect_request("")
-    assert_equal("", response.headers["location"])
+    assert_redirects("", {
+      :frontend_prefix_routes_to_path => "",
+      :frontend_prefix_routes_to_root => "",
+      :frontend_root_routes_to_path => "",
+      :frontend_prefix_equals_backend_prefix => "",
+      :frontend_prefix_contains_backend_prefix => "",
+      :backend_prefix_contains_frontend_prefix => "",
+    })
   end
 
   private
 
   def make_redirect_request(redirect_to)
-    response = Typhoeus.get("http://127.0.0.1:9080/#{unique_test_class_id}/front/end/path/redirect", http_options.deep_merge({
-      :headers => {
-        "Host" => "frontend.foo",
-      },
-      :params => {
-        :to => redirect_to,
-      },
-    }))
-    assert_response_code(302, response)
-    response
+    responses = {}
+
+    {
+      :frontend_prefix_routes_to_path => "/frontend-prefix-routes-to-path/redirect",
+      :frontend_prefix_routes_to_root => "/frontend-prefix-routes-to-root/redirect",
+      :frontend_root_routes_to_path => "/redirect",
+      :frontend_prefix_equals_backend_prefix => "/backend-prefix/redirect",
+      :frontend_prefix_contains_backend_prefix => "/redirect/frontend-prefix-contains-backend-prefix/frontend-piece/",
+      :backend_prefix_contains_frontend_prefix => "/redirect/backend-prefix-contains-frontend-prefix/",
+    }.each do |key, path|
+      response = Typhoeus.get("http://127.0.0.1:9080#{path}", http_options.deep_merge({
+        :headers => {
+          "Host" => unique_test_class_hostname,
+        },
+        :params => {
+          :to => redirect_to,
+        },
+      }))
+      assert_response_code(302, response)
+      responses[key] = response
+    end
+
+    responses
+  end
+
+  def assert_redirects(redirect_to, expected_redirects)
+    responses = make_redirect_request(redirect_to)
+    actual_redirects = {}
+    responses.each do |key, response|
+      actual_redirects[key] = response.headers["Location"]
+    end
+
+    assert_equal(expected_redirects, actual_redirects)
   end
 end
diff --git a/test/support/api_umbrella_test_helpers/common_asserts.rb b/test/support/api_umbrella_test_helpers/common_asserts.rb
index 329c3ed7a..cff6d4fea 100644
--- a/test/support/api_umbrella_test_helpers/common_asserts.rb
+++ b/test/support/api_umbrella_test_helpers/common_asserts.rb
@@ -16,6 +16,7 @@ def assert_response_code(expected_code, response)
           redirect_time: #{response.redirect_time}
           effective_url: #{response.effective_url}
           primary_ip: #{response.primary_ip}
+          response_headers: #{response.headers.inspect}
           response_body: #{response.body}
         EOS
       end
diff --git a/test/support/api_umbrella_test_helpers/setup.rb b/test/support/api_umbrella_test_helpers/setup.rb
index 33d80de6c..c4c2b0c25 100644
--- a/test/support/api_umbrella_test_helpers/setup.rb
+++ b/test/support/api_umbrella_test_helpers/setup.rb
@@ -8,6 +8,7 @@ module Setup
 
     include ApiUmbrellaTestHelpers::CommonAsserts
 
+    @@incrementing_unique_number = 0
     @@incrementing_unique_ip_addr = IPAddr.new("127.0.0.1")
     @@current_override_config = {}
     mattr_reader :api_user
@@ -22,8 +23,11 @@ module Setup
     mattr_accessor(:config_mutex) { Mutex.new }
     mattr_accessor(:config_set_mutex) { Mutex.new }
     mattr_accessor(:config_publish_mutex) { Mutex.new }
+    mattr_accessor(:increment_mutex) { Mutex.new }
 
     included do
+      mattr_accessor :unique_test_class_id_value
+      mattr_accessor :unique_test_class_hostname_value
       mattr_accessor :class_setup_complete
       mattr_accessor(:class_setup_mutex) { Mutex.new }
     end
@@ -271,41 +275,59 @@ def override_config_reset(reload_flag)
       override_config_set({}, reload_flag)
     end
 
-    def unique_test_class_id
-      @unique_test_class_id ||= self.class.name.gsub(/[^\w]+/, "-")
+    def to_unique_id(name)
+      name.gsub(/[^\w]+/, "-")
     end
 
-    def unique_test_id
-      @unique_test_id ||= self.location.gsub(/[^\w]+/, "-")
+    def to_unique_hostname(name)
+      # Replace all non alpha-numeric chars (namely underscores that might be
+      # in the ID) with dashes (since underscores aren't valid for hostnames).
+      hostname = name.downcase.gsub(/[^a-z0-9]+/, "-")
+
+      # Truncate the hostname so the label will fit in unbound's 63 char limit.
+      hostname = hostname[-56..-1] || hostname
+
+      # Strip first char if it happens to be a dash.
+      hostname.gsub!(/^-/, "")
+
+      # Since we've truncated the test ID, it's possible it's no longer unique,
+      # so append a unique number to the end (ensuring that it will fit within
+      # the 63 char limit).
+      unique_number = next_unique_number
+      assert_operator(unique_number, :<=, 999999)
+      hostname = "#{hostname}-#{unique_number.to_s.rjust(6, "0")}"
+
+      "#{hostname}.test"
     end
 
-    def unique_test_hostname
-      unless @unique_test_hostname
-        # Replace all non alpha-numeric chars (namely underscores that might be
-        # in the ID) with dashes (since underscores aren't valid for
-        # hostnames).
-        hostname = unique_test_id.downcase.gsub(/[^a-z0-9]+/, "-")
+    def unique_test_class_id
+      self.unique_test_class_id_value ||= to_unique_id(self.class.name)
+    end
 
-        # Truncate the hostname so the label will fit in unbound's 63 char
-        # limit.
-        hostname = hostname[-56..-1] || hostname
+    def unique_test_class_hostname
+      self.unique_test_class_hostname_value ||= to_unique_hostname(unique_test_class_id)
+    end
 
-        # Strip first char if it happens to be a dash.
-        hostname.gsub!(/^-/, "")
+    def unique_test_id
+      @unique_test_id ||= to_unique_id(self.location)
+    end
 
-        # Since we've truncated the test ID, it's possible it's no longer
-        # unique, so append some random chars (but still, fitting within the 63
-        # char limit).
-        hostname = "#{hostname}-#{SecureRandom.hex(3)}"
+    def unique_test_hostname
+      @unique_test_hostname ||= to_unique_hostname(unique_test_id)
+    end
 
-        @unique_test_hostname = "#{hostname}.test"
+    def next_unique_number
+      self.increment_mutex.synchronize do
+        @@incrementing_unique_number += 1
+        @@incrementing_unique_number
       end
-      @unique_test_hostname
     end
 
     def next_unique_ip_addr
-      @@incrementing_unique_ip_addr = @@incrementing_unique_ip_addr.succ
-      @@incrementing_unique_ip_addr.to_s
+      self.increment_mutex.synchronize do
+        @@incrementing_unique_ip_addr = @@incrementing_unique_ip_addr.succ
+        @@incrementing_unique_ip_addr.to_s
+      end
     end
 
     def unique_test_ip_addr