diff --git a/go.mod b/go.mod
index 2d88d57..fee2bba 100644
--- a/go.mod
+++ b/go.mod
@@ -6,6 +6,8 @@ require (
 	github.com/Luzifer/rconfig/v2 v2.3.0
 	github.com/aws/aws-sdk-go v1.40.30
 	github.com/cheggaaa/pb v1.0.29
+	github.com/gofrs/uuid v4.1.0+incompatible
+	github.com/gosimple/slug v1.11.0
 	github.com/pkg/errors v0.9.1
 	github.com/rivo/uniseg v0.2.0 // indirect
 	github.com/sirupsen/logrus v1.8.1
@@ -13,6 +15,7 @@ require (
 
 require (
 	github.com/Luzifer/rconfig v1.2.0 // indirect
+	github.com/gosimple/unidecode v1.0.0 // indirect
 	github.com/jmespath/go-jmespath v0.4.0 // indirect
 	github.com/mattn/go-runewidth v0.0.13 // indirect
 	github.com/onsi/ginkgo v1.16.4 // indirect
diff --git a/go.sum b/go.sum
index 7efa8bf..1a1a724 100644
--- a/go.sum
+++ b/go.sum
@@ -15,6 +15,8 @@ github.com/fsnotify/fsnotify v1.4.7/go.mod h1:jwhsz4b93w/PPRr/qN1Yymfu8t87LnFCMo
 github.com/fsnotify/fsnotify v1.4.9 h1:hsms1Qyu0jgnwNXIxa+/V/PDsU6CfLf6CNO8H7IWoS4=
 github.com/fsnotify/fsnotify v1.4.9/go.mod h1:znqG4EE+3YCdAaPaxE2ZRY/06pZUdp0tY4IgpuI1SZQ=
 github.com/go-task/slim-sprig v0.0.0-20210107165309-348f09dbbbc0/go.mod h1:fyg7847qk6SyHyPtNmDHnmrv/HOrqktSC+C9fM+CJOE=
+github.com/gofrs/uuid v4.1.0+incompatible h1:sIa2eCvUTwgjbqXrPLfNwUf9S3i3mpH1O1atV+iL/Wk=
+github.com/gofrs/uuid v4.1.0+incompatible/go.mod h1:b2aQJv3Z4Fp6yNu3cdSllBxTCLRxnplIgP/c0N/04lM=
 github.com/golang/protobuf v1.2.0/go.mod h1:6lQm79b+lXiMfvg/cZm0SGofjICqVBUtrP5yJMmIC1U=
 github.com/golang/protobuf v1.4.0-rc.1/go.mod h1:ceaxUfeHdC40wWswd/P6IGgMaK3YpKi5j83Wpe3EHw8=
 github.com/golang/protobuf v1.4.0-rc.1.0.20200221234624-67d41d38c208/go.mod h1:xKAWHe0F5eneWXFV3EuXVDTCmh+JuBKY0li0aMyXATA=
@@ -28,6 +30,10 @@ github.com/google/go-cmp v0.3.0/go.mod h1:8QqcDgzrUqlUb/G2PQTWiueGozuR1884gddMyw
 github.com/google/go-cmp v0.3.1/go.mod h1:8QqcDgzrUqlUb/G2PQTWiueGozuR1884gddMywk6iLU=
 github.com/google/go-cmp v0.4.0/go.mod h1:v8dTdLbMG2kIc/vJvl+f65V22dbkXbowE6jgT/gNBxE=
 github.com/google/go-cmp v0.5.5/go.mod h1:v8dTdLbMG2kIc/vJvl+f65V22dbkXbowE6jgT/gNBxE=
+github.com/gosimple/slug v1.11.0 h1:QkFeOkXIEDvvtIt++P7cUuO4G9PZVQEgLuYbYZzawMA=
+github.com/gosimple/slug v1.11.0/go.mod h1:MICb3w495l9KNdZm+Xn5b6T2Hn831f9DMxiJ1r+bAjw=
+github.com/gosimple/unidecode v1.0.0 h1:kPdvM+qy0tnk4/BrnkrbdJ82xe88xn7c9hcaipDz4dQ=
+github.com/gosimple/unidecode v1.0.0/go.mod h1:CP0Cr1Y1kogOtx0bJblKzsVWrqYaqfNOnHzpgWw4Awc=
 github.com/hpcloud/tail v1.0.0/go.mod h1:ab1qPbhIpdTxEkNHXyeSf5vhxWSCs/tWer42PpOxQnU=
 github.com/jmespath/go-jmespath v0.4.0 h1:BEgLn5cpjn8UN1mAw4NjwDrS35OdebyEtFe+9YPoQUg=
 github.com/jmespath/go-jmespath v0.4.0/go.mod h1:T8mJZnbsbmF+m6zOOFylbeCJqk5+pHWvzYPziyZiYoo=
diff --git a/main.go b/main.go
index 470d4b8..51fc3e6 100644
--- a/main.go
+++ b/main.go
@@ -17,12 +17,13 @@ import (
 
 var (
 	cfg = struct {
-		BaseURL        string `flag:"base-url" env:"BASE_URL" default:"" description:"URL to prepend before filename"`
-		BasePath       string `flag:"base-path" env:"BASE_PATH" default:"file/{{ printf \"%.6s\" .Hash }}" description:"Path to upload the file to"`
+		BaseURL        string `flag:"base-url" default:"" description:"URL to prepend before filename"`
+		BasePath       string `flag:"base-path" default:"" description:"DEPRECATED: Path to upload the file to"`
 		Bootstrap      bool   `flag:"bootstrap" default:"false" description:"Upload frontend files into bucket"`
-		Bucket         string `flag:"bucket" env:"BUCKET" default:"" description:"S3 bucket to upload files to" validate:"nonzero"`
-		ContentType    string `flag:"content-type,c" default:"" description:"Force content-type to be set to this value"`
-		Listen         string `flag:"listen" env:"LISTEN" default:"" description:"Enable HTTP server if set to IP/Port (e.g. ':3000')"`
+		Bucket         string `flag:"bucket" default:"" description:"S3 bucket to upload files to" validate:"nonzero"`
+		ContentType    string `flag:"content-type,c" vardefault:"file_template" description:"Force content-type to be set to this value"`
+		FileTemplate   string `flag:"file-template" default:"" description:"Full name template of the uploaded file"`
+		Listen         string `flag:"listen" default:"" description:"Enable HTTP server if set to IP/Port (e.g. ':3000')"`
 		Progress       bool   `flag:"progress" default:"false" description:"Show progress bar while uploading"`
 		VersionAndExit bool   `flag:"version" default:"false" description:"Prints current version and exits"`
 	}{}
@@ -33,8 +34,12 @@ var (
 	version = "dev"
 )
 
-func init() {
+func initApp() {
 	rconfig.AutoEnv(true)
+	rconfig.SetVariableDefaults(map[string]string{
+		"file_template": `file/{{ printf "%.6s" .Hash }}/{{ .SafeFileName }}`,
+	})
+
 	if err := rconfig.ParseAndValidate(&cfg); err != nil {
 		log.Fatalf("Unable to parse commandline options: %s", err)
 	}
@@ -43,9 +48,16 @@ func init() {
 		fmt.Printf("share %s\n", version)
 		os.Exit(0)
 	}
+
+	if cfg.BasePath != "" {
+		cfg.FileTemplate = strings.Join([]string{strings.TrimRight(cfg.BasePath, "/"), `{{ .SafeFileName }}`}, "/")
+		log.WithField("file-template", cfg.FileTemplate).Warn("Using deprecated base-path parameter! Using update file-template...")
+	}
 }
 
 func main() {
+	initApp()
+
 	switch {
 
 	case cfg.Bootstrap:
@@ -81,10 +93,12 @@ func doCLIUpload() error {
 	inFileName := rconfig.Args()[1]
 
 	if inFileName == "-" {
-		inFileName = "stdin"
 		if cfg.ContentType == "" {
 			// If we don't have an explicitly set content-type assume stdin contains text
+			inFileName = "stdin"
 			cfg.ContentType = "text/plain"
+		} else if ext, err := mimeResolver.ExtensionsByType(cfg.ContentType); err == nil {
+			inFileName = strings.Join([]string{"stdin", ext}, "")
 		}
 
 		// Stdin is not seekable, so we need to buffer it
diff --git a/mime.go b/mime.go
new file mode 100644
index 0000000..ce9dc0e
--- /dev/null
+++ b/mime.go
@@ -0,0 +1,37 @@
+package main
+
+import (
+	"mime"
+	"strings"
+
+	"github.com/pkg/errors"
+)
+
+type mimeDB map[string]string
+
+// mimeResolver contains some well-known mime-types and falls back
+// to mime package to resolve the extension if no internal override
+// is known for the given mime-type
+var mimeResolver = mimeDB{
+	"text/plain": ".txt", // Detected as .asc when using mime package
+}
+
+func (m mimeDB) ExtensionsByType(t string) (string, error) {
+	if v, ok := m[t]; ok {
+		return v, nil
+	}
+
+	exts, err := mime.ExtensionsByType(t)
+	if err != nil {
+		return "", err
+	}
+
+	for _, ext := range exts {
+		if !strings.HasPrefix(ext, ".") {
+			continue
+		}
+		return ext, nil
+	}
+
+	return "", errors.New("no extension found")
+}
diff --git a/upload.go b/upload.go
index 7a2353a..3728044 100644
--- a/upload.go
+++ b/upload.go
@@ -17,6 +17,8 @@ import (
 	"github.com/aws/aws-sdk-go/aws/session"
 	"github.com/aws/aws-sdk-go/service/s3"
 	"github.com/cheggaaa/pb"
+	"github.com/gofrs/uuid"
+	"github.com/gosimple/slug"
 	"github.com/pkg/errors"
 	log "github.com/sirupsen/logrus"
 )
@@ -101,18 +103,22 @@ func executeUpload(inFileName string, inFileHandle io.ReadSeeker, useCalculatedF
 }
 
 func calculateUploadFilename(inFile string, inFileHandle io.ReadSeeker) (string, error) {
-	upFile := path.Join(
-		cfg.BasePath,
-		strings.Replace(path.Base(inFile), " ", "_", -1),
-	)
-
 	fileHash, err := hashFile(inFileHandle)
 	if err != nil {
 		return "", err
 	}
 
-	return executeTemplate(upFile, map[string]interface{}{
-		"Hash": fileHash,
+	safeFileName := strings.Join([]string{
+		slug.Make(strings.TrimSuffix(path.Base(inFile), path.Ext(inFile))),
+		path.Ext(inFile),
+	}, "")
+
+	return executeTemplate(cfg.FileTemplate, map[string]interface{}{
+		"Ext":          path.Ext(inFile),
+		"FileName":     path.Base(inFile),
+		"Hash":         fileHash,
+		"SafeFileName": safeFileName,
+		"UUID":         uuid.Must(uuid.NewV4()).String(),
 	})
 }
 
@@ -130,7 +136,7 @@ func hashFile(inFileHandle io.ReadSeeker) (string, error) {
 }
 
 func executeTemplate(tplStr string, vars map[string]interface{}) (string, error) {
-	tpl, err := template.New("basepath").Parse(tplStr)
+	tpl, err := template.New("filename").Parse(tplStr)
 	if err != nil {
 		return "", err
 	}