diff --git a/internal/api/client/fileserver/servefile.go b/internal/api/client/fileserver/servefile.go
index 0858af3ce..236a2d8ac 100644
--- a/internal/api/client/fileserver/servefile.go
+++ b/internal/api/client/fileserver/servefile.go
@@ -85,20 +85,22 @@ func (m *FileServer) ServeFile(c *gin.Context) {
 		return
 	}
 
+	defer func() {
+		// if the content is a ReadCloser (ie., it's streamed from storage), close it when we're done
+		if content.Content != nil {
+			if closer, ok := content.Content.(io.ReadCloser); ok {
+				if err := closer.Close(); err != nil {
+					log.Errorf("ServeFile: error closing readcloser: %s", err)
+				}
+			}
+		}
+	}()
+
 	if content.URL != nil {
 		c.Redirect(http.StatusFound, content.URL.String())
 		return
 	}
 
-	defer func() {
-		// if the content is a ReadCloser, close it when we're done
-		if closer, ok := content.Content.(io.ReadCloser); ok {
-			if err := closer.Close(); err != nil {
-				log.Errorf("ServeFile: error closing readcloser: %s", err)
-			}
-		}
-	}()
-
 	// TODO: if the requester only accepts text/html we should try to serve them *something*.
 	// This is mostly needed because when sharing a link to a gts-hosted file on something like mastodon, the masto servers will
 	// attempt to look up the content to provide a preview of the link, and they ask for text/html.
diff --git a/internal/media/processingemoji.go b/internal/media/processingemoji.go
index 121f54ddc..e3ed5ce0a 100644
--- a/internal/media/processingemoji.go
+++ b/internal/media/processingemoji.go
@@ -121,6 +121,12 @@ func (p *ProcessingEmoji) loadStatic(ctx context.Context) error {
 			return p.err
 		}
 
+		defer func() {
+			if err := stored.Close(); err != nil {
+				log.Errorf("loadStatic: error closing stored full size: %s", err)
+			}
+		}()
+
 		// we haven't processed a static version of this emoji yet so do it now
 		static, err := deriveStaticEmoji(stored, p.emoji.ImageContentType)
 		if err != nil {
@@ -129,12 +135,6 @@ func (p *ProcessingEmoji) loadStatic(ctx context.Context) error {
 			return p.err
 		}
 
-		if err := stored.Close(); err != nil {
-			p.err = fmt.Errorf("loadStatic: error closing stored full size: %s", err)
-			atomic.StoreInt32(&p.staticState, int32(errored))
-			return p.err
-		}
-
 		// put the static in storage
 		if err := p.storage.Put(ctx, p.emoji.ImageStaticPath, static.small); err != nil {
 			p.err = fmt.Errorf("loadStatic: error storing static: %s", err)
diff --git a/internal/media/processingmedia.go b/internal/media/processingmedia.go
index 26fbc0cea..3f3a68f3f 100644
--- a/internal/media/processingmedia.go
+++ b/internal/media/processingmedia.go
@@ -145,9 +145,7 @@ func (p *ProcessingMedia) loadThumb(ctx context.Context) error {
 			return p.err
 		}
 
-		// whatever happens, close the stream when we're done
 		defer func() {
-			log.Tracef("loadThumb: closing stored stream %s", p.attachment.URL)
 			if err := stored.Close(); err != nil {
 				log.Errorf("loadThumb: error closing stored full size: %s", err)
 			}
@@ -210,6 +208,12 @@ func (p *ProcessingMedia) loadFullSize(ctx context.Context) error {
 			return p.err
 		}
 
+		defer func() {
+			if err := stored.Close(); err != nil {
+				log.Errorf("loadFullSize: error closing stored full size: %s", err)
+			}
+		}()
+
 		// decode the image
 		ct := p.attachment.File.ContentType
 		switch ct {
@@ -227,12 +231,6 @@ func (p *ProcessingMedia) loadFullSize(ctx context.Context) error {
 			return p.err
 		}
 
-		if err := stored.Close(); err != nil {
-			p.err = fmt.Errorf("loadFullSize: error closing stored full size: %s", err)
-			atomic.StoreInt32(&p.fullSizeState, int32(errored))
-			return p.err
-		}
-
 		// set appropriate fields on the attachment based on the image we derived
 		p.attachment.FileMeta.Original = gtsmodel.Original{
 			Width:  decoded.width,
diff --git a/internal/router/router.go b/internal/router/router.go
index da00b685d..d66e5f9cd 100644
--- a/internal/router/router.go
+++ b/internal/router/router.go
@@ -21,6 +21,7 @@ package router
 import (
 	"context"
 	"fmt"
+	"net"
 	"net/http"
 	"time"
 
@@ -37,6 +38,7 @@ const (
 	writeTimeout      = 30 * time.Second
 	idleTimeout       = 30 * time.Second
 	readHeaderTimeout = 30 * time.Second
+	shutdownTimeout   = 30 * time.Second
 )
 
 // Router provides the REST interface for gotosocial, using gin.
@@ -128,7 +130,16 @@ func (r *router) Start() {
 
 // Stop shuts down the router nicely
 func (r *router) Stop(ctx context.Context) error {
-	return r.srv.Shutdown(ctx)
+	log.Infof("shutting down http router with %s grace period", shutdownTimeout)
+	timeout, cancel := context.WithTimeout(ctx, shutdownTimeout)
+	defer cancel()
+
+	if err := r.srv.Shutdown(timeout); err != nil {
+		return fmt.Errorf("error shutting down http router: %s", err)
+	}
+
+	log.Info("http router closed connections and shut down gracefully")
+	return nil
 }
 
 // New returns a new Router with the specified configuration.
@@ -174,17 +185,24 @@ func New(ctx context.Context, db db.DB) (Router, error) {
 		return nil, err
 	}
 
-	// create the http server here, passing the gin engine as handler
+	// use the passed-in command context as the base context for the server,
+	// since we'll never want the server to live past the command anyway
+	baseCtx := func(_ net.Listener) context.Context {
+		return ctx
+	}
+
 	bindAddress := config.GetBindAddress()
 	port := config.GetPort()
-	listen := fmt.Sprintf("%s:%d", bindAddress, port)
+	addr := fmt.Sprintf("%s:%d", bindAddress, port)
+
 	s := &http.Server{
-		Addr:              listen,
-		Handler:           engine,
+		Addr:              addr,
+		Handler:           engine, // use gin engine as handler
 		ReadTimeout:       readTimeout,
+		ReadHeaderTimeout: readHeaderTimeout,
 		WriteTimeout:      writeTimeout,
 		IdleTimeout:       idleTimeout,
-		ReadHeaderTimeout: readHeaderTimeout,
+		BaseContext:       baseCtx,
 	}
 
 	// We need to spawn the underlying server slightly differently depending on whether lets encrypt is enabled or not.