diff --git a/server/handler/try.go b/server/handler/try.go
index 47054eb..6cfe08e 100644
--- a/server/handler/try.go
+++ b/server/handler/try.go
@@ -39,43 +39,8 @@ func tryUpstream(ctx *context.Context, giteaClient *gitea.Client,
 	// Add host for debugging.
 	options.Host = trimmedHost
 
-	// Check for redirects
-	redirects := options.GetRedirects(giteaClient, redirectsCache)
-	if len(redirects) > 0 {
-		for _, redirect := range redirects {
-			reqUrl := ctx.Req.RequestURI
-			trimmedFromUrl := strings.TrimSuffix(redirect.From, "/*")
-			if strings.TrimSuffix(redirect.From, "/") == strings.TrimSuffix(reqUrl, "/") {
-				if redirect.StatusCode == 200 {
-					options.TargetPath = redirect.To
-				} else {
-					ctx.Redirect(redirect.To, redirect.StatusCode)
-					return
-				}
-			}
-			if strings.HasSuffix(redirect.From, "/*") && strings.HasPrefix(reqUrl, trimmedFromUrl) {
-				if strings.Contains(redirect.To, ":splat") {
-					splatUrl := strings.ReplaceAll(redirect.To, ":splat", strings.TrimPrefix(reqUrl, trimmedFromUrl))
-					if redirect.StatusCode == 200 {
-						options.TargetPath = splatUrl
-					} else {
-						ctx.Redirect(splatUrl, redirect.StatusCode)
-						return
-					}
-				} else {
-					if redirect.StatusCode == 200 {
-						options.TargetPath = redirect.To
-					} else {
-						ctx.Redirect(redirect.To, redirect.StatusCode)
-						return
-					}
-				}
-			}
-		}
-	}
-
 	// Try to request the file from the Gitea API
-	if !options.Upstream(ctx, giteaClient) {
+	if !options.Upstream(ctx, giteaClient, redirectsCache) {
 		html.ReturnErrorPage(ctx, "", ctx.StatusCode)
 	}
 }
diff --git a/server/upstream/redirects.go b/server/upstream/redirects.go
index f27aed4..a48ffe4 100644
--- a/server/upstream/redirects.go
+++ b/server/upstream/redirects.go
@@ -25,9 +25,11 @@ const redirectsConfig = "_redirects"
 func (o *Options) GetRedirects(giteaClient *gitea.Client, redirectsCache cache.SetGetKey) []Redirect {
 	var redirects []Redirect
 
+	// Check for cached redirects
 	if cachedValue, ok := redirectsCache.Get(o.TargetOwner + "/" + o.TargetRepo + "/" + o.TargetBranch); ok {
 		redirects = cachedValue.([]Redirect)
 	} else {
+		// Get _redirects file and parse
 		body, err := giteaClient.GiteaRawContent(o.TargetOwner, o.TargetRepo, o.TargetBranch, redirectsConfig)
 		if err == nil {
 			for _, line := range strings.Split(string(body), "\n") {
diff --git a/server/upstream/upstream.go b/server/upstream/upstream.go
index 3845969..38dc6c8 100644
--- a/server/upstream/upstream.go
+++ b/server/upstream/upstream.go
@@ -11,6 +11,7 @@ import (
 	"github.com/rs/zerolog/log"
 
 	"codeberg.org/codeberg/pages/html"
+	"codeberg.org/codeberg/pages/server/cache"
 	"codeberg.org/codeberg/pages/server/context"
 	"codeberg.org/codeberg/pages/server/gitea"
 )
@@ -52,7 +53,7 @@ type Options struct {
 }
 
 // Upstream requests a file from the Gitea API at GiteaRoot and writes it to the request context.
-func (o *Options) Upstream(ctx *context.Context, giteaClient *gitea.Client) (final bool) {
+func (o *Options) Upstream(ctx *context.Context, giteaClient *gitea.Client, redirectsCache cache.SetGetKey) (final bool) {
 	log := log.With().Strs("upstream", []string{o.TargetOwner, o.TargetRepo, o.TargetBranch, o.TargetPath}).Logger()
 
 	if o.TargetOwner == "" || o.TargetRepo == "" {
@@ -110,7 +111,7 @@ func (o *Options) Upstream(ctx *context.Context, giteaClient *gitea.Client) (fin
 			optionsForIndexPages.appendTrailingSlash = true
 			for _, indexPage := range upstreamIndexPages {
 				optionsForIndexPages.TargetPath = strings.TrimSuffix(o.TargetPath, "/") + "/" + indexPage
-				if optionsForIndexPages.Upstream(ctx, giteaClient) {
+				if optionsForIndexPages.Upstream(ctx, giteaClient, redirectsCache) {
 					return true
 				}
 			}
@@ -118,7 +119,7 @@ func (o *Options) Upstream(ctx *context.Context, giteaClient *gitea.Client) (fin
 			optionsForIndexPages.appendTrailingSlash = false
 			optionsForIndexPages.redirectIfExists = strings.TrimSuffix(ctx.Path(), "/") + ".html"
 			optionsForIndexPages.TargetPath = o.TargetPath + ".html"
-			if optionsForIndexPages.Upstream(ctx, giteaClient) {
+			if optionsForIndexPages.Upstream(ctx, giteaClient, redirectsCache) {
 				return true
 			}
 		}
@@ -131,11 +132,60 @@ func (o *Options) Upstream(ctx *context.Context, giteaClient *gitea.Client) (fin
 			optionsForNotFoundPages.appendTrailingSlash = false
 			for _, notFoundPage := range upstreamNotFoundPages {
 				optionsForNotFoundPages.TargetPath = "/" + notFoundPage
-				if optionsForNotFoundPages.Upstream(ctx, giteaClient) {
+				if optionsForNotFoundPages.Upstream(ctx, giteaClient, redirectsCache) {
 					return true
 				}
 			}
 		}
+
+		// Check for redirects
+		redirects := o.GetRedirects(giteaClient, redirectsCache)
+		if len(redirects) > 0 {
+			for _, redirect := range redirects {
+				reqUrl := ctx.Req.RequestURI
+
+				// check if from url matches request url
+				if strings.TrimSuffix(redirect.From, "/") == strings.TrimSuffix(reqUrl, "/") {
+					// do rewrite if status code is 200
+					if redirect.StatusCode == 200 {
+						o.TargetPath = redirect.To
+						o.Upstream(ctx, giteaClient, redirectsCache)
+						return true
+					} else {
+						ctx.Redirect(redirect.To, redirect.StatusCode)
+						return true
+					}
+				}
+
+				// handle wildcard redirects
+				trimmedFromUrl := strings.TrimSuffix(redirect.From, "/*")
+				if strings.HasSuffix(redirect.From, "/*") && strings.HasPrefix(reqUrl, trimmedFromUrl) {
+					if strings.Contains(redirect.To, ":splat") {
+						splatUrl := strings.ReplaceAll(redirect.To, ":splat", strings.TrimPrefix(reqUrl, trimmedFromUrl))
+						// do rewrite if status code is 200
+						if redirect.StatusCode == 200 {
+							o.TargetPath = splatUrl
+							o.Upstream(ctx, giteaClient, redirectsCache)
+							return true
+						} else {
+							ctx.Redirect(splatUrl, redirect.StatusCode)
+							return true
+						}
+					} else {
+						// do rewrite if status code is 200
+						if redirect.StatusCode == 200 {
+							o.TargetPath = redirect.To
+							o.Upstream(ctx, giteaClient, redirectsCache)
+							return true
+						} else {
+							ctx.Redirect(redirect.To, redirect.StatusCode)
+							return true
+						}
+					}
+				}
+			}
+		}
+
 		return false
 	}