diff --git a/go.mod b/go.mod
index e0c11bb5fb..afbedf22f2 100644
--- a/go.mod
+++ b/go.mod
@@ -595,6 +595,7 @@ require (
 	github.com/inconshreveable/mousetrap v1.1.0 // indirect
 	github.com/jackmordaunt/icns/v3 v3.0.1 // indirect
 	github.com/jbenet/go-context v0.0.0-20150711004518-d14ea06fba99 // indirect
+	github.com/joho/godotenv v1.5.1
 	github.com/kaptinlin/go-i18n v0.2.4 // indirect
 	github.com/kaptinlin/jsonpointer v0.4.10 // indirect
 	github.com/kaptinlin/jsonschema v0.6.10 // indirect
diff --git a/go.sum b/go.sum
index 644911e5ec..a290649c90 100644
--- a/go.sum
+++ b/go.sum
@@ -768,6 +768,8 @@ github.com/jedib0t/go-pretty/v6 v6.7.1/go.mod h1:YwC5CE4fJ1HFUDeivSV1r//AmANFHyq
 github.com/jessevdk/go-flags v1.4.0/go.mod h1:4FA24M0QyGHXBuZZK/XkWh8h0e1EYbRYJSGM75WSRxI=
 github.com/jmoiron/sqlx v1.4.0 h1:1PLqN7S1UYp5t4SrVVnt4nUVNemrDAtxlulVe+Qgm3o=
 github.com/jmoiron/sqlx v1.4.0/go.mod h1:ZrZ7UsYB/weZdl2Bxg6jCRO9c3YHl8r3ahlKmRT4JLY=
+github.com/joho/godotenv v1.5.1 h1:7eLL/+HRGLY0ldzfGMeQkb7vMd0as4CfYvUVzLqw0N0=
+github.com/joho/godotenv v1.5.1/go.mod h1:f4LDr5Voq0i2e/R5DDNOoa2zzDfwtkZa6DnEwAbqwq4=
 github.com/josharian/intern v1.0.0 h1:vlS4z54oSdjm0bgjRigI+G1HpF+tI+9rE5LLzOg8HmY=
 github.com/josharian/intern v1.0.0/go.mod h1:5DoeVV0s6jJacbCEi61lwdGj/aVlrQvzHFFd8Hwg//Y=
 github.com/josharian/native v1.1.1-0.20230202152459-5c7d0dd6ab86 h1:elKwZS1OcdQ0WwEDBeqxKwb7WB62QX8bvZ/FJnVXIfk=
diff --git a/scripts/develop/main.go b/scripts/develop/main.go
index b6905af7cf..e66f6f0936 100644
--- a/scripts/develop/main.go
+++ b/scripts/develop/main.go
@@ -27,6 +27,7 @@ import (
 	"time"
 
 	"github.com/google/uuid"
+	"github.com/joho/godotenv"
 	"golang.org/x/sync/errgroup"
 	"golang.org/x/xerrors"
 
@@ -69,6 +70,24 @@ const (
 )
 
 func main() {
+	// Pre-parse --env-file before serpent runs so that variables from
+	// the file are visible to serpent's Env-tag resolution for other
+	// options. The flag is also registered in the serpent OptionSet
+	// below for --help discoverability.
+	envFile, err := parseEnvFileFlag()
+	if err != nil {
+		_, _ = fmt.Fprintf(os.Stderr, "develop: %v\n", err)
+		os.Exit(1)
+	}
+	if envFile != "" {
+		n, err := loadEnvFile(envFile)
+		if err != nil {
+			_, _ = fmt.Fprintf(os.Stderr, "develop: error loading env file %s: %v\n", envFile, err)
+			os.Exit(1)
+		}
+		_, _ = fmt.Fprintf(os.Stderr, "develop: loaded %d variable(s) from %s\n", n, envFile)
+	}
+
 	var cfg devConfig
 
 	cmd := &serpent.Command{
@@ -182,6 +201,12 @@ func main() {
 				Description: "Accept changed migration files and update tracking. Use when you've manually fixed the DB to match the new migrations.",
 				Value:       serpent.BoolOf(&cfg.dbContinue),
 			},
+			{
+				Flag:        "env-file",
+				Env:         "CODER_DEV_ENV_FILE",
+				Description: "Path to a .env file to load before starting. Variables in the file do not override existing environment variables. Note: unquoted and double-quoted values undergo $VAR expansion against other entries in the same file (not the process environment); use single quotes for literal dollar signs.",
+				Value:       serpent.StringOf(&cfg.envFile),
+			},
 		},
 		Handler: func(inv *serpent.Invocation) error {
 			cfg.serverExtraArgs = inv.Args
@@ -198,7 +223,7 @@ func main() {
 		},
 	}
 
-	err := cmd.Invoke(os.Args[1:]...).WithOS().Run()
+	err = cmd.Invoke(os.Args[1:]...).WithOS().Run()
 	if err != nil {
 		_, _ = fmt.Fprintf(os.Stderr, "error: %v\n", err)
 		os.Exit(1)
@@ -223,6 +248,9 @@ type devConfig struct {
 	dbRollback        bool
 	dbReset           bool
 	dbContinue        bool
+	// envFile is populated by serpent for --help output; actual loading
+	// uses parseEnvFileFlag() before serpent runs.
+	envFile           string
 	projectRoot       string
 	binaryPath        string
 	configDir         string
@@ -435,8 +463,46 @@ func (c *devConfig) cmd(ctx context.Context, bin string, args ...string) *exec.C
 	return cmd
 }
 
-// filterEnv returns env with any variables whose key matches
-// exclude removed.
+// parseEnvFileFlag extracts the --env-file value from os.Args and
+// CODER_DEV_ENV_FILE before serpent runs, so that loaded variables
+// are visible to serpent's Env-tag resolution for other options.
+func parseEnvFileFlag() (string, error) {
+	for i, arg := range os.Args[1:] {
+		if arg == "--env-file" {
+			if i+2 >= len(os.Args) {
+				return "", xerrors.New("--env-file requires a value")
+			}
+			return os.Args[i+2], nil
+		}
+		if v, ok := strings.CutPrefix(arg, "--env-file="); ok {
+			return v, nil
+		}
+	}
+	return os.Getenv("CODER_DEV_ENV_FILE"), nil
+}
+
+// loadEnvFile reads the file at path using godotenv and sets any variables
+// not already present in the process environment. It returns the number of
+// variables set.
+func loadEnvFile(path string) (int, error) {
+	vars, err := godotenv.Read(path)
+	if err != nil {
+		return 0, err
+	}
+	var n int
+	for key, val := range vars {
+		if _, exists := os.LookupEnv(key); exists {
+			continue
+		}
+		if err := os.Setenv(key, val); err != nil {
+			return n, err
+		}
+		n++
+	}
+	return n, nil
+}
+
+// filterEnv returns env with any variables whose key matches exclude removed.
 func filterEnv(env []string, exclude ...string) []string {
 	out := make([]string, 0, len(env))
 	for _, e := range env {
diff --git a/scripts/develop/main_test.go b/scripts/develop/main_test.go
index 98bcd79f06..2491d52b4c 100644
--- a/scripts/develop/main_test.go
+++ b/scripts/develop/main_test.go
@@ -855,3 +855,134 @@ func TestPrometheusBannerEntry(t *testing.T) {
 		})
 	}
 }
+
+//nolint:paralleltest // loadEnvFile mutates process-global environment.
+func TestLoadEnvFile(t *testing.T) {
+	t.Run("LoadsVariablesFromFile", func(t *testing.T) {
+		tmpDir := t.TempDir()
+		envFile := filepath.Join(tmpDir, ".env")
+		err := os.WriteFile(envFile, []byte(strings.Join([]string{
+			"# Comment line",
+			"",
+			"FOO_TEST_VAR=bar",
+			"export BAZ_TEST_VAR=qux",
+			`QUOTED_TEST_VAR="hello world"`,
+			"SINGLE_QUOTED_TEST_VAR='single quoted'",
+		}, "\n")), 0o600)
+		require.NoError(t, err)
+
+		// Ensure none are set beforehand.
+		t.Setenv("FOO_TEST_VAR", "")
+		os.Unsetenv("FOO_TEST_VAR")
+		t.Setenv("BAZ_TEST_VAR", "")
+		os.Unsetenv("BAZ_TEST_VAR")
+		t.Setenv("QUOTED_TEST_VAR", "")
+		os.Unsetenv("QUOTED_TEST_VAR")
+		t.Setenv("SINGLE_QUOTED_TEST_VAR", "")
+		os.Unsetenv("SINGLE_QUOTED_TEST_VAR")
+
+		n, err := loadEnvFile(envFile)
+		require.NoError(t, err)
+		assert.Equal(t, 4, n)
+		assert.Equal(t, "bar", os.Getenv("FOO_TEST_VAR"))
+		assert.Equal(t, "qux", os.Getenv("BAZ_TEST_VAR"))
+		assert.Equal(t, "hello world", os.Getenv("QUOTED_TEST_VAR"))
+		assert.Equal(t, "single quoted", os.Getenv("SINGLE_QUOTED_TEST_VAR"))
+	})
+
+	t.Run("DoesNotOverrideExisting", func(t *testing.T) {
+		tmpDir := t.TempDir()
+		envFile := filepath.Join(tmpDir, ".env")
+		err := os.WriteFile(envFile, []byte("EXISTING_TEST_VAR=new\n"), 0o600)
+		require.NoError(t, err)
+
+		t.Setenv("EXISTING_TEST_VAR", "original")
+
+		n, err := loadEnvFile(envFile)
+		require.NoError(t, err)
+		assert.Equal(t, 0, n)
+		assert.Equal(t, "original", os.Getenv("EXISTING_TEST_VAR"))
+	})
+
+	t.Run("ErrorsOnMissingFile", func(t *testing.T) {
+		_, err := loadEnvFile("/nonexistent/path/.env")
+		require.Error(t, err)
+	})
+
+	t.Run("ErrorsOnEmptyPath", func(t *testing.T) {
+		// This tests the caller logic (main), but we verify loadEnvFile
+		// would error on empty path since godotenv.Read("") fails.
+		_, err := loadEnvFile("")
+		require.Error(t, err)
+	})
+}
+
+//nolint:paralleltest // parseEnvFileFlag mutates process-global os.Args.
+func TestParseEnvFileFlag(t *testing.T) {
+	t.Run("FlagWithSpace", func(t *testing.T) {
+		orig := os.Args
+		t.Cleanup(func() { os.Args = orig })
+		os.Args = []string{"develop", "--env-file", "/tmp/test.env", "--port", "3000"}
+
+		result, err := parseEnvFileFlag()
+		require.NoError(t, err)
+		assert.Equal(t, "/tmp/test.env", result)
+	})
+
+	t.Run("FlagWithEquals", func(t *testing.T) {
+		orig := os.Args
+		t.Cleanup(func() { os.Args = orig })
+		os.Args = []string{"develop", "--env-file=/tmp/test.env", "--port", "3000"}
+
+		result, err := parseEnvFileFlag()
+		require.NoError(t, err)
+		assert.Equal(t, "/tmp/test.env", result)
+	})
+
+	t.Run("FallsBackToEnvVar", func(t *testing.T) {
+		orig := os.Args
+		t.Cleanup(func() { os.Args = orig })
+		os.Args = []string{"develop", "--port", "3000"}
+
+		t.Setenv("CODER_DEV_ENV_FILE", "/tmp/from-env.env")
+
+		result, err := parseEnvFileFlag()
+		require.NoError(t, err)
+		assert.Equal(t, "/tmp/from-env.env", result)
+	})
+
+	t.Run("FlagTakesPrecedenceOverEnvVar", func(t *testing.T) {
+		orig := os.Args
+		t.Cleanup(func() { os.Args = orig })
+		os.Args = []string{"develop", "--env-file", "/tmp/from-flag.env"}
+
+		t.Setenv("CODER_DEV_ENV_FILE", "/tmp/from-env.env")
+
+		result, err := parseEnvFileFlag()
+		require.NoError(t, err)
+		assert.Equal(t, "/tmp/from-flag.env", result)
+	})
+
+	t.Run("ReturnsEmptyWhenUnset", func(t *testing.T) {
+		orig := os.Args
+		t.Cleanup(func() { os.Args = orig })
+		os.Args = []string{"develop", "--port", "3000"}
+
+		t.Setenv("CODER_DEV_ENV_FILE", "")
+		os.Unsetenv("CODER_DEV_ENV_FILE")
+
+		result, err := parseEnvFileFlag()
+		require.NoError(t, err)
+		assert.Equal(t, "", result)
+	})
+
+	t.Run("ErrorsWhenValueMissing", func(t *testing.T) {
+		orig := os.Args
+		t.Cleanup(func() { os.Args = orig })
+		os.Args = []string{"develop", "--env-file"}
+
+		_, err := parseEnvFileFlag()
+		require.Error(t, err)
+		assert.Contains(t, err.Error(), "--env-file requires a value")
+	})
+}