diff --git a/internal/inspect/detectors/pyshiny.go b/internal/inspect/detectors/pyshiny.go
new file mode 100644
index 000000000..485ac46fb
--- /dev/null
+++ b/internal/inspect/detectors/pyshiny.go
@@ -0,0 +1,81 @@
+package detectors
+
+// Copyright (C) 2023 by Posit Software, PBC.
+
+import (
+	"fmt"
+	"regexp"
+	"strings"
+
+	"github.com/rstudio/connect-client/internal/config"
+	"github.com/rstudio/connect-client/internal/util"
+)
+
+type pyShinyDetector struct {
+	inferenceHelper
+}
+
+func NewPyShinyDetector() *pyShinyDetector {
+	return &pyShinyDetector{
+		inferenceHelper: defaultInferenceHelper{},
+	}
+}
+
+var shinyExpressImportRE = regexp.MustCompile(`(import\s+shiny.express)|(from\s+shiny.express\s+import)|(from\s+shiny\s+import.*\bexpress\b)`)
+
+func hasShinyExpressImport(content string) bool {
+	return shinyExpressImportRE.MatchString(content)
+}
+
+func fileHasShinyExpressImport(path util.Path) (bool, error) {
+	content, err := path.ReadFile()
+	if err != nil {
+		return false, err
+	}
+	return hasShinyExpressImport(string(content)), nil
+}
+
+var invalidPythonIdentifierRE = regexp.MustCompile(`(^[0-9]|[^A-Za-z0-9])`)
+
+func shinyExpressEntrypoint(entrypoint string) string {
+	module := strings.TrimSuffix(entrypoint, ".py")
+
+	safeEntrypoint := invalidPythonIdentifierRE.ReplaceAllStringFunc(module, func(match string) string {
+		return fmt.Sprintf("_%x_", int(match[0]))
+	})
+	return "shiny.express.app:" + safeEntrypoint
+}
+
+func (d *pyShinyDetector) InferType(path util.Path) (*config.Config, error) {
+	entrypoint, entrypointPath, err := d.InferEntrypoint(path, ".py", "main.py", "app.py")
+	if err != nil {
+		return nil, err
+	}
+	if entrypoint == "" {
+		// We didn't find a matching filename
+		return nil, nil
+	}
+	matches, err := d.FileHasPythonImports(entrypointPath, []string{"shiny"})
+	if err != nil {
+		return nil, err
+	}
+	if !matches {
+		// Not a PyShiny app
+		return nil, nil
+	}
+	isShinyExpress, err := fileHasShinyExpressImport(entrypointPath)
+	if err != nil {
+		return nil, err
+	}
+	cfg := config.New()
+
+	if isShinyExpress {
+		cfg.Entrypoint = shinyExpressEntrypoint(entrypoint)
+	} else {
+		cfg.Entrypoint = entrypoint
+	}
+	cfg.Type = config.ContentTypePythonShiny
+	// indicate that Python inspection is needed
+	cfg.Python = &config.Python{}
+	return cfg, nil
+}
diff --git a/internal/inspect/detectors/pyshiny_test.go b/internal/inspect/detectors/pyshiny_test.go
new file mode 100644
index 000000000..dfdb95348
--- /dev/null
+++ b/internal/inspect/detectors/pyshiny_test.go
@@ -0,0 +1,66 @@
+package detectors
+
+// Copyright (C) 2023 by Posit Software, PBC.
+
+import (
+	"testing"
+
+	"github.com/rstudio/connect-client/internal/config"
+	"github.com/rstudio/connect-client/internal/schema"
+	"github.com/rstudio/connect-client/internal/util"
+	"github.com/rstudio/connect-client/internal/util/utiltest"
+	"github.com/spf13/afero"
+	"github.com/stretchr/testify/suite"
+)
+
+type PyShinySuite struct {
+	utiltest.Suite
+}
+
+func TestPyShinySuite(t *testing.T) {
+	suite.Run(t, new(PyShinySuite))
+}
+
+func (s *PyShinySuite) TestInferType() {
+	base := util.NewPath("/project", afero.NewMemMapFs())
+	err := base.MkdirAll(0777)
+	s.NoError(err)
+
+	filename := "app.py"
+	path := base.Join(filename)
+	err = path.WriteFile([]byte("import shiny\n"), 0600)
+	s.Nil(err)
+
+	detector := NewPyShinyDetector()
+	t, err := detector.InferType(base)
+	s.Nil(err)
+	s.Equal(&config.Config{
+		Schema:     schema.ConfigSchemaURL,
+		Type:       config.ContentTypePythonShiny,
+		Entrypoint: filename,
+		Validate:   true,
+		Python:     &config.Python{},
+	}, t)
+}
+
+func (s *PyShinySuite) TestInferTypeShinyExpress() {
+	base := util.NewPath("/project", afero.NewMemMapFs())
+	err := base.MkdirAll(0777)
+	s.NoError(err)
+
+	filename := "app.py"
+	path := base.Join(filename)
+	err = path.WriteFile([]byte("import shiny.express\n"), 0600)
+	s.Nil(err)
+
+	detector := NewPyShinyDetector()
+	t, err := detector.InferType(base)
+	s.Nil(err)
+	s.Equal(&config.Config{
+		Schema:     schema.ConfigSchemaURL,
+		Type:       config.ContentTypePythonShiny,
+		Entrypoint: "shiny.express.app:app",
+		Validate:   true,
+		Python:     &config.Python{},
+	}, t)
+}
diff --git a/internal/inspect/detectors/python.go b/internal/inspect/detectors/python.go
index 5f9b82147..08fc0f12c 100644
--- a/internal/inspect/detectors/python.go
+++ b/internal/inspect/detectors/python.go
@@ -60,12 +60,6 @@ func NewBokehDetector() *PythonAppDetector {
 	})
 }
 
-func NewPyShinyDetector() *PythonAppDetector {
-	return NewPythonAppDetector(config.ContentTypePythonShiny, []string{
-		"shiny",
-	})
-}
-
 func (d *PythonAppDetector) InferType(path util.Path) (*config.Config, error) {
 	entrypoint, entrypointPath, err := d.InferEntrypoint(
 		path, ".py", "main.py", "app.py", "streamlit_app.py", "api.py")