diff --git a/caddy/setup/rewrite.go b/caddy/setup/rewrite.go
index b510a237b..c70a2f94d 100644
--- a/caddy/setup/rewrite.go
+++ b/caddy/setup/rewrite.go
@@ -1,6 +1,8 @@
 package setup
 
 import (
+	"net/http"
+
 	"github.com/mholt/caddy/middleware"
 	"github.com/mholt/caddy/middleware/rewrite"
 )
@@ -13,7 +15,11 @@ func Rewrite(c *Controller) (middleware.Middleware, error) {
 	}
 
 	return func(next middleware.Handler) middleware.Handler {
-		return rewrite.Rewrite{Next: next, Rules: rewrites}
+		return rewrite.Rewrite{
+			Next:    next,
+			FileSys: http.Dir(c.Root),
+			Rules:   rewrites,
+		}
 	}, nil
 }
 
@@ -30,6 +36,8 @@ func rewriteParse(c *Controller) ([]rewrite.Rule, error) {
 
 		args := c.RemainingArgs()
 
+		var ifs []rewrite.If
+
 		switch len(args) {
 		case 2:
 			rule = rewrite.NewSimpleRule(args[0], args[1])
@@ -56,6 +64,16 @@ func rewriteParse(c *Controller) ([]rewrite.Rule, error) {
 						return nil, c.ArgErr()
 					}
 					ext = args1
+				case "if":
+					args1 := c.RemainingArgs()
+					if len(args1) != 3 {
+						return nil, c.ArgErr()
+					}
+					ifCond, err := rewrite.NewIf(args1[0], args1[1], args1[2])
+					if err != nil {
+						return nil, err
+					}
+					ifs = append(ifs, ifCond)
 				default:
 					return nil, c.ArgErr()
 				}
@@ -64,7 +82,7 @@ func rewriteParse(c *Controller) ([]rewrite.Rule, error) {
 			if pattern == "" || to == "" {
 				return nil, c.ArgErr()
 			}
-			if rule, err = rewrite.NewRegexpRule(base, pattern, to, ext); err != nil {
+			if rule, err = rewrite.NewComplexRule(base, pattern, to, ext, ifs); err != nil {
 				return nil, err
 			}
 			regexpRules = append(regexpRules, rule)
diff --git a/caddy/setup/rewrite_test.go b/caddy/setup/rewrite_test.go
index f54266788..ddef7cd49 100644
--- a/caddy/setup/rewrite_test.go
+++ b/caddy/setup/rewrite_test.go
@@ -98,14 +98,14 @@ func TestRewriteParse(t *testing.T) {
 			r	.*
 			to	/to
 		 }`, false, []rewrite.Rule{
-			&rewrite.RegexpRule{Base: "/", To: "/to", Regexp: regexp.MustCompile(".*")},
+			&rewrite.ComplexRule{Base: "/", To: "/to", Regexp: regexp.MustCompile(".*")},
 		}},
 		{`rewrite {
 			regexp	.*
 			to		/to
 			ext		/ html txt
 		 }`, false, []rewrite.Rule{
-			&rewrite.RegexpRule{Base: "/", To: "/to", Exts: []string{"/", "html", "txt"}, Regexp: regexp.MustCompile(".*")},
+			&rewrite.ComplexRule{Base: "/", To: "/to", Exts: []string{"/", "html", "txt"}, Regexp: regexp.MustCompile(".*")},
 		}},
 		{`rewrite /path {
 			r	rr
@@ -116,26 +116,26 @@ func TestRewriteParse(t *testing.T) {
 		 	to 		/to
 		 }
 		 `, false, []rewrite.Rule{
-			&rewrite.RegexpRule{Base: "/path", To: "/dest", Regexp: regexp.MustCompile("rr")},
-			&rewrite.RegexpRule{Base: "/", To: "/to", Regexp: regexp.MustCompile("[a-z]+")},
+			&rewrite.ComplexRule{Base: "/path", To: "/dest", Regexp: regexp.MustCompile("rr")},
+			&rewrite.ComplexRule{Base: "/", To: "/to", Regexp: regexp.MustCompile("[a-z]+")},
 		}},
 		{`rewrite {
 			to	/to
 		 }`, true, []rewrite.Rule{
-			&rewrite.RegexpRule{},
+			&rewrite.ComplexRule{},
 		}},
 		{`rewrite {
 			r	.*
 		 }`, true, []rewrite.Rule{
-			&rewrite.RegexpRule{},
+			&rewrite.ComplexRule{},
 		}},
 		{`rewrite {
 
 		 }`, true, []rewrite.Rule{
-			&rewrite.RegexpRule{},
+			&rewrite.ComplexRule{},
 		}},
 		{`rewrite /`, true, []rewrite.Rule{
-			&rewrite.RegexpRule{},
+			&rewrite.ComplexRule{},
 		}},
 	}
 
@@ -157,8 +157,8 @@ func TestRewriteParse(t *testing.T) {
 		}
 
 		for j, e := range test.expected {
-			actualRule := actual[j].(*rewrite.RegexpRule)
-			expectedRule := e.(*rewrite.RegexpRule)
+			actualRule := actual[j].(*rewrite.ComplexRule)
+			expectedRule := e.(*rewrite.ComplexRule)
 
 			if actualRule.Base != expectedRule.Base {
 				t.Errorf("Test %d, rule %d: Expected Base=%s, got %s",
diff --git a/middleware/rewrite/condition.go b/middleware/rewrite/condition.go
new file mode 100644
index 000000000..ab69ef4af
--- /dev/null
+++ b/middleware/rewrite/condition.go
@@ -0,0 +1,110 @@
+package rewrite
+
+import (
+	"fmt"
+	"github.com/mholt/caddy/middleware"
+	"net/http"
+	"regexp"
+	"strings"
+)
+
+const (
+	// Operators
+	Is         = "is"
+	Not        = "not"
+	Has        = "has"
+	StartsWith = "starts_with"
+	EndsWith   = "ends_with"
+	Match      = "match"
+)
+
+func operatorError(operator string) error {
+	return fmt.Errorf("Invalid operator", operator)
+}
+
+func newReplacer(r *http.Request) middleware.Replacer {
+	return middleware.NewReplacer(r, nil, "")
+}
+
+// condition is a rewrite condition.
+type condition func(string, string) bool
+
+var conditions = map[string]condition{
+	Is:         isFunc,
+	Not:        notFunc,
+	Has:        hasFunc,
+	StartsWith: startsWithFunc,
+	EndsWith:   endsWithFunc,
+	Match:      matchFunc,
+}
+
+// isFunc is condition for Is operator.
+// It checks for equality.
+func isFunc(a, b string) bool {
+	return a == b
+}
+
+// notFunc is condition for Not operator.
+// It checks for inequality.
+func notFunc(a, b string) bool {
+	return a != b
+}
+
+// hasFunc is condition for Has operator.
+// It checks if b is a substring of a.
+func hasFunc(a, b string) bool {
+	return strings.Contains(a, b)
+}
+
+// startsWithFunc is condition for StartsWith operator.
+// It checks if b is a prefix of a.
+func startsWithFunc(a, b string) bool {
+	return strings.HasPrefix(a, b)
+}
+
+// endsWithFunc is condition for EndsWith operator.
+// It checks if b is a suffix of a.
+func endsWithFunc(a, b string) bool {
+	return strings.HasSuffix(a, b)
+}
+
+// matchFunc is condition for Match operator.
+// It does regexp matching of
+func matchFunc(a, b string) bool {
+	matched, _ := regexp.MatchString(b, a)
+	return matched
+}
+
+// If is statement for a rewrite condition.
+type If struct {
+	A        string
+	Operator string
+	B        string
+}
+
+// True returns true if the condition is true and false otherwise.
+// If r is not nil, it replaces placeholders before comparison.
+func (i If) True(r *http.Request) bool {
+	if c, ok := conditions[i.Operator]; ok {
+		a, b := i.A, i.B
+		if r != nil {
+			replacer := newReplacer(r)
+			a = replacer.Replace(i.A)
+			b = replacer.Replace(i.B)
+		}
+		return c(a, b)
+	}
+	return false
+}
+
+// NewIf creates a new If condition.
+func NewIf(a, operator, b string) (If, error) {
+	if _, ok := conditions[operator]; !ok {
+		return If{}, operatorError(operator)
+	}
+	return If{
+		A:        a,
+		Operator: operator,
+		B:        b,
+	}, nil
+}
diff --git a/middleware/rewrite/rewrite.go b/middleware/rewrite/rewrite.go
index 88944f73d..cc60e82cd 100644
--- a/middleware/rewrite/rewrite.go
+++ b/middleware/rewrite/rewrite.go
@@ -5,7 +5,6 @@ package rewrite
 import (
 	"fmt"
 	"net/http"
-	"net/url"
 	"path"
 	"path/filepath"
 	"regexp"
@@ -16,14 +15,15 @@ import (
 
 // Rewrite is middleware to rewrite request locations internally before being handled.
 type Rewrite struct {
-	Next  middleware.Handler
-	Rules []Rule
+	Next    middleware.Handler
+	FileSys http.FileSystem
+	Rules   []Rule
 }
 
 // ServeHTTP implements the middleware.Handler interface.
 func (rw Rewrite) ServeHTTP(w http.ResponseWriter, r *http.Request) (int, error) {
 	for _, rule := range rw.Rules {
-		if ok := rule.Rewrite(r); ok {
+		if ok := rule.Rewrite(rw.FileSys, r); ok {
 			break
 		}
 	}
@@ -33,7 +33,7 @@ func (rw Rewrite) ServeHTTP(w http.ResponseWriter, r *http.Request) (int, error)
 // Rule describes an internal location rewrite rule.
 type Rule interface {
 	// Rewrite rewrites the internal location of the current request.
-	Rewrite(*http.Request) bool
+	Rewrite(http.FileSystem, *http.Request) bool
 }
 
 // SimpleRule is a simple rewrite rule.
@@ -47,23 +47,20 @@ func NewSimpleRule(from, to string) SimpleRule {
 }
 
 // Rewrite rewrites the internal location of the current request.
-func (s SimpleRule) Rewrite(r *http.Request) bool {
+func (s SimpleRule) Rewrite(fs http.FileSystem, r *http.Request) bool {
 	if s.From == r.URL.Path {
 		// take note of this rewrite for internal use by fastcgi
 		// all we need is the URI, not full URL
 		r.Header.Set(headerFieldName, r.URL.RequestURI())
 
-		// replace variables
-		to := path.Clean(middleware.NewReplacer(r, nil, "").Replace(s.To))
-
-		r.URL.Path = to
-		return true
+		// attempt rewrite
+		return To(fs, r, s.To)
 	}
 	return false
 }
 
-// RegexpRule is a rewrite rule based on a regular expression
-type RegexpRule struct {
+// ComplexRule is a rewrite rule based on a regular expression
+type ComplexRule struct {
 	// Path base. Request to this path and subpaths will be rewritten
 	Base string
 
@@ -73,18 +70,26 @@ type RegexpRule struct {
 	// Extensions to filter by
 	Exts []string
 
+	// Rewrite conditions
+	Ifs []If
+
 	*regexp.Regexp
 }
 
 // NewRegexpRule creates a new RegexpRule. It returns an error if regexp
 // pattern (pattern) or extensions (ext) are invalid.
-func NewRegexpRule(base, pattern, to string, ext []string) (*RegexpRule, error) {
-	r, err := regexp.Compile(pattern)
-	if err != nil {
-		return nil, err
+func NewComplexRule(base, pattern, to string, ext []string, ifs []If) (*ComplexRule, error) {
+	// validate regexp if present
+	var r *regexp.Regexp
+	if pattern != "" {
+		var err error
+		r, err = regexp.Compile(pattern)
+		if err != nil {
+			return nil, err
+		}
 	}
 
-	// validate extensions
+	// validate extensions if present
 	for _, v := range ext {
 		if len(v) < 2 || (len(v) < 3 && v[0] == '!') {
 			// check if no extension is specified
@@ -94,16 +99,17 @@ func NewRegexpRule(base, pattern, to string, ext []string) (*RegexpRule, error)
 		}
 	}
 
-	return &RegexpRule{
-		base,
-		to,
-		ext,
-		r,
+	return &ComplexRule{
+		Base:   base,
+		To:     to,
+		Exts:   ext,
+		Ifs:    ifs,
+		Regexp: r,
 	}, nil
 }
 
 // Rewrite rewrites the internal location of the current request.
-func (r *RegexpRule) Rewrite(req *http.Request) bool {
+func (r *ComplexRule) Rewrite(fs http.FileSystem, req *http.Request) bool {
 	rPath := req.URL.Path
 
 	// validate base
@@ -127,31 +133,13 @@ func (r *RegexpRule) Rewrite(req *http.Request) bool {
 		return false
 	}
 
-	// replace variables
-	to := path.Clean(middleware.NewReplacer(req, nil, "").Replace(r.To))
-
-	// validate resulting path
-	url, err := url.Parse(to)
-	if err != nil {
-		return false
-	}
-
-	// take note of this rewrite for internal use by fastcgi
-	// all we need is the URI, not full URL
-	req.Header.Set(headerFieldName, req.URL.RequestURI())
-
-	// perform rewrite
-	req.URL.Path = url.Path
-	if url.RawQuery != "" {
-		// overwrite query string if present
-		req.URL.RawQuery = url.RawQuery
-	}
-	return true
+	// attempt rewrite
+	return To(fs, req, r.To)
 }
 
 // matchExt matches rPath against registered file extensions.
 // Returns true if a match is found and false otherwise.
-func (r *RegexpRule) matchExt(rPath string) bool {
+func (r *ComplexRule) matchExt(rPath string) bool {
 	f := filepath.Base(rPath)
 	ext := path.Ext(f)
 	if ext == "" {
diff --git a/middleware/rewrite/rewrite_test.go b/middleware/rewrite/rewrite_test.go
index fb0470262..ca4cc5128 100644
--- a/middleware/rewrite/rewrite_test.go
+++ b/middleware/rewrite/rewrite_test.go
@@ -4,9 +4,8 @@ import (
 	"fmt"
 	"net/http"
 	"net/http/httptest"
-	"testing"
-
 	"strings"
+	"testing"
 
 	"github.com/mholt/caddy/middleware"
 )
@@ -38,7 +37,7 @@ func TestRewrite(t *testing.T) {
 		if s := strings.Split(regexpRule[3], "|"); len(s) > 1 {
 			ext = s[:len(s)-1]
 		}
-		rule, err := NewRegexpRule(regexpRule[0], regexpRule[1], regexpRule[2], ext)
+		rule, err := NewComplexRule(regexpRule[0], regexpRule[1], regexpRule[2], ext)
 		if err != nil {
 			t.Fatal(err)
 		}
diff --git a/middleware/rewrite/to.go b/middleware/rewrite/to.go
new file mode 100644
index 000000000..0ee8a1595
--- /dev/null
+++ b/middleware/rewrite/to.go
@@ -0,0 +1,68 @@
+package rewrite
+
+import (
+	"log"
+	"net/http"
+	"net/url"
+	"strings"
+)
+
+// To attempts rewrite. It attempts to rewrite to first valid path
+// or the last path if none of the paths are valid.
+// Returns true if rewrite is successful and false otherwise.
+func To(fs http.FileSystem, r *http.Request, to string) bool {
+	tos := strings.Fields(to)
+	replacer := newReplacer(r)
+
+	// try each rewrite paths
+	t := ""
+	for _, v := range tos {
+		t = replacer.Replace(v)
+		if isValidFile(fs, t) {
+			break
+		}
+	}
+
+	// validate resulting path
+	u, err := url.Parse(t)
+	if err != nil {
+		// Let the user know we got here. Rewrite is expected but
+		// the resulting url is invalid.
+		log.Printf("[ERROR] rewrite: resulting path '%v' is invalid. error: %v", t, err)
+		return false
+	}
+
+	// take note of this rewrite for internal use by fastcgi
+	// all we need is the URI, not full URL
+	r.Header.Set(headerFieldName, r.URL.RequestURI())
+
+	// perform rewrite
+	r.URL.Path = u.Path
+	if u.RawQuery != "" {
+		// overwrite query string if present
+		r.URL.RawQuery = u.RawQuery
+	}
+	if u.Fragment != "" {
+		// overwrite fragment if present
+		r.URL.Fragment = u.Fragment
+	}
+
+	return true
+}
+
+// isValidFile checks if file exists on the filesystem.
+// if file ends with `/`, it is validated as a directory.
+func isValidFile(fs http.FileSystem, file string) bool {
+	f, err := fs.Open(file)
+	if err != nil {
+		return false
+	}
+	defer f.Close()
+
+	stat, err := f.Stat()
+	if err != nil {
+		return false
+	}
+
+	return strings.HasSuffix(file, "/") && stat.IsDir()
+}