diff --git a/extensions/auth-machine/pkg/config/parser/parse.go b/extensions/auth-machine/pkg/config/parser/parse.go
index feea7ec41..8b12cb877 100644
--- a/extensions/auth-machine/pkg/config/parser/parse.go
+++ b/extensions/auth-machine/pkg/config/parser/parse.go
@@ -2,11 +2,11 @@ package parser
 
 import (
 	"errors"
-	"fmt"
 
 	"github.com/owncloud/ocis/extensions/auth-machine/pkg/config"
 	"github.com/owncloud/ocis/extensions/auth-machine/pkg/config/defaults"
 	ociscfg "github.com/owncloud/ocis/ocis-pkg/config"
+	"github.com/owncloud/ocis/ocis-pkg/shared"
 
 	"github.com/owncloud/ocis/ocis-pkg/config/envdecode"
 )
@@ -35,7 +35,7 @@ func ParseConfig(cfg *config.Config) error {
 
 func Validate(cfg *config.Config) error {
 	if cfg.AuthProviders.Machine.APIKey == "" {
-		return fmt.Errorf("machine auth api key is not set up properly, bailing out (%s)", cfg.Service.Name)
+		return shared.MissingMachineAuthApiKeyError(cfg.Service.Name)
 	}
 	return nil
 }
diff --git a/extensions/frontend/pkg/config/parser/parse.go b/extensions/frontend/pkg/config/parser/parse.go
index c71a8e583..ffc09565f 100644
--- a/extensions/frontend/pkg/config/parser/parse.go
+++ b/extensions/frontend/pkg/config/parser/parse.go
@@ -2,11 +2,11 @@ package parser
 
 import (
 	"errors"
-	"fmt"
 
 	"github.com/owncloud/ocis/extensions/frontend/pkg/config"
 	"github.com/owncloud/ocis/extensions/frontend/pkg/config/defaults"
 	ociscfg "github.com/owncloud/ocis/ocis-pkg/config"
+	"github.com/owncloud/ocis/ocis-pkg/shared"
 
 	"github.com/owncloud/ocis/ocis-pkg/config/envdecode"
 )
@@ -35,7 +35,7 @@ func ParseConfig(cfg *config.Config) error {
 
 func Validate(cfg *config.Config) error {
 	if cfg.TransferSecret == "" {
-		return fmt.Errorf("reva transfer secret is not set up properly, bailing out (%s)", cfg.Service.Name)
+		return shared.MissingRevaTransferSecretError(cfg.Service.Name)
 	}
 
 	return nil
diff --git a/extensions/gateway/pkg/config/parser/parse.go b/extensions/gateway/pkg/config/parser/parse.go
index 2a0a4e069..237f3037d 100644
--- a/extensions/gateway/pkg/config/parser/parse.go
+++ b/extensions/gateway/pkg/config/parser/parse.go
@@ -2,11 +2,11 @@ package parser
 
 import (
 	"errors"
-	"fmt"
 
 	"github.com/owncloud/ocis/extensions/gateway/pkg/config"
 	"github.com/owncloud/ocis/extensions/gateway/pkg/config/defaults"
 	ociscfg "github.com/owncloud/ocis/ocis-pkg/config"
+	"github.com/owncloud/ocis/ocis-pkg/shared"
 
 	"github.com/owncloud/ocis/ocis-pkg/config/envdecode"
 )
@@ -35,7 +35,7 @@ func ParseConfig(cfg *config.Config) error {
 
 func Validate(cfg *config.Config) error {
 	if cfg.TransferSecret == "" {
-		return fmt.Errorf("reva transfer secret is not set up properly, bailing out (%s)", cfg.Service.Name)
+		return shared.MissingRevaTransferSecretError(cfg.Service.Name)
 	}
 
 	return nil
diff --git a/extensions/notifications/pkg/config/parser/parse.go b/extensions/notifications/pkg/config/parser/parse.go
index fddb96b24..aec697154 100644
--- a/extensions/notifications/pkg/config/parser/parse.go
+++ b/extensions/notifications/pkg/config/parser/parse.go
@@ -2,11 +2,11 @@ package parser
 
 import (
 	"errors"
-	"fmt"
 
 	"github.com/owncloud/ocis/extensions/notifications/pkg/config"
 	"github.com/owncloud/ocis/extensions/notifications/pkg/config/defaults"
 	ociscfg "github.com/owncloud/ocis/ocis-pkg/config"
+	"github.com/owncloud/ocis/ocis-pkg/shared"
 
 	"github.com/owncloud/ocis/ocis-pkg/config/envdecode"
 )
@@ -35,7 +35,7 @@ func ParseConfig(cfg *config.Config) error {
 
 func Validate(cfg *config.Config) error {
 	if cfg.Notifications.MachineAuthAPIKey == "" {
-		return fmt.Errorf("machine auth api key is not set up properly, bailing out (%s)", cfg.Service.Name)
+		return shared.MissingMachineAuthApiKeyError(cfg.Service.Name)
 	}
 	return nil
 }
diff --git a/extensions/ocs/pkg/config/parser/parse.go b/extensions/ocs/pkg/config/parser/parse.go
index ce253edd1..28074ada3 100644
--- a/extensions/ocs/pkg/config/parser/parse.go
+++ b/extensions/ocs/pkg/config/parser/parse.go
@@ -2,11 +2,12 @@ package parser
 
 import (
 	"errors"
-	"fmt"
 
 	"github.com/owncloud/ocis/extensions/ocs/pkg/config"
 	"github.com/owncloud/ocis/extensions/ocs/pkg/config/defaults"
+
 	ociscfg "github.com/owncloud/ocis/ocis-pkg/config"
+	"github.com/owncloud/ocis/ocis-pkg/shared"
 
 	"github.com/owncloud/ocis/ocis-pkg/config/envdecode"
 )
@@ -35,7 +36,7 @@ func ParseConfig(cfg *config.Config) error {
 
 func Validate(cfg *config.Config) error {
 	if cfg.MachineAuthAPIKey == "" {
-		return fmt.Errorf("machine auth api key is not set up properly, bailing out (%s)", cfg.Service.Name)
+		return shared.MissingMachineAuthApiKeyError(cfg.Service.Name)
 	}
 	return nil
 }
diff --git a/extensions/proxy/pkg/config/parser/parse.go b/extensions/proxy/pkg/config/parser/parse.go
index 5f15fb293..22b96257e 100644
--- a/extensions/proxy/pkg/config/parser/parse.go
+++ b/extensions/proxy/pkg/config/parser/parse.go
@@ -2,11 +2,11 @@ package parser
 
 import (
 	"errors"
-	"fmt"
 
 	"github.com/owncloud/ocis/extensions/proxy/pkg/config"
 	"github.com/owncloud/ocis/extensions/proxy/pkg/config/defaults"
 	ociscfg "github.com/owncloud/ocis/ocis-pkg/config"
+	"github.com/owncloud/ocis/ocis-pkg/shared"
 
 	"github.com/owncloud/ocis/ocis-pkg/config/envdecode"
 )
@@ -34,7 +34,7 @@ func ParseConfig(cfg *config.Config) error {
 
 func Validate(cfg *config.Config) error {
 	if cfg.MachineAuthAPIKey == "" {
-		return fmt.Errorf("machine auth api key is not set up properly, bailing out (%s)", cfg.Service.Name)
+		return shared.MissingMachineAuthApiKeyError(cfg.Service.Name)
 	}
 
 	return nil
diff --git a/extensions/sharing/pkg/config/parser/parse.go b/extensions/sharing/pkg/config/parser/parse.go
index 84a09cc6d..27ccd4657 100644
--- a/extensions/sharing/pkg/config/parser/parse.go
+++ b/extensions/sharing/pkg/config/parser/parse.go
@@ -2,11 +2,11 @@ package parser
 
 import (
 	"errors"
-	"fmt"
 
 	"github.com/owncloud/ocis/extensions/sharing/pkg/config"
 	"github.com/owncloud/ocis/extensions/sharing/pkg/config/defaults"
 	ociscfg "github.com/owncloud/ocis/ocis-pkg/config"
+	"github.com/owncloud/ocis/ocis-pkg/shared"
 
 	"github.com/owncloud/ocis/ocis-pkg/config/envdecode"
 )
@@ -35,11 +35,11 @@ func ParseConfig(cfg *config.Config) error {
 
 func Validate(cfg *config.Config) error {
 	if cfg.PublicSharingDrivers.CS3.MachineAuthAPIKey == "" {
-		return fmt.Errorf("machine auth api key for the cs3 public sharing driver is not set up properly, bailing out (%s)", cfg.Service.Name)
+		return shared.MissingMachineAuthApiKeyError(cfg.Service.Name)
 	}
 
 	if cfg.UserSharingDrivers.CS3.MachineAuthAPIKey == "" {
-		return fmt.Errorf("machine auth api key for the cs3 user sharing driver is not set up properly, bailing out (%s)", cfg.Service.Name)
+		return shared.MissingMachineAuthApiKeyError(cfg.Service.Name)
 	}
 
 	return nil
diff --git a/extensions/storage/pkg/config/parser/parse.go b/extensions/storage/pkg/config/parser/parse.go
index bf30c761f..5cf17d1c4 100644
--- a/extensions/storage/pkg/config/parser/parse.go
+++ b/extensions/storage/pkg/config/parser/parse.go
@@ -2,11 +2,11 @@ package parser
 
 import (
 	"errors"
-	"fmt"
 
 	"github.com/owncloud/ocis/extensions/storage-metadata/pkg/config"
 	"github.com/owncloud/ocis/extensions/storage-metadata/pkg/config/defaults"
 	ociscfg "github.com/owncloud/ocis/ocis-pkg/config"
+	"github.com/owncloud/ocis/ocis-pkg/shared"
 
 	"github.com/owncloud/ocis/ocis-pkg/config/envdecode"
 )
@@ -35,7 +35,7 @@ func ParseConfig(cfg *config.Config) error {
 
 func Validate(cfg *config.Config) error {
 	if cfg.TransferSecret == "" {
-		return fmt.Errorf("reva transfer secret is not set up properly, bailing out (storage)")
+		return shared.MissingRevaTransferSecretError(cfg.Service.Name)
 	}
 	return nil
 }
diff --git a/extensions/thumbnails/pkg/config/parser/parse.go b/extensions/thumbnails/pkg/config/parser/parse.go
index 625705dd5..fd2079281 100644
--- a/extensions/thumbnails/pkg/config/parser/parse.go
+++ b/extensions/thumbnails/pkg/config/parser/parse.go
@@ -2,11 +2,11 @@ package parser
 
 import (
 	"errors"
-	"fmt"
 
 	"github.com/owncloud/ocis/extensions/thumbnails/pkg/config"
 	"github.com/owncloud/ocis/extensions/thumbnails/pkg/config/defaults"
 	ociscfg "github.com/owncloud/ocis/ocis-pkg/config"
+	"github.com/owncloud/ocis/ocis-pkg/shared"
 
 	"github.com/owncloud/ocis/ocis-pkg/config/envdecode"
 )
@@ -36,7 +36,7 @@ func ParseConfig(cfg *config.Config) error {
 
 func Validate(cfg *config.Config) error {
 	if cfg.Thumbnail.TransferSecret == "" {
-		return fmt.Errorf("reva transfer secret is not set up properly, bailing out (%s)", cfg.Service.Name)
+		return shared.MissingRevaTransferSecretError(cfg.Service.Name)
 	}
 
 	return nil
diff --git a/ocis-pkg/config/parser/parse.go b/ocis-pkg/config/parser/parse.go
index f9d0a7c7b..3c4939a23 100644
--- a/ocis-pkg/config/parser/parse.go
+++ b/ocis-pkg/config/parser/parse.go
@@ -2,7 +2,6 @@ package parser
 
 import (
 	"errors"
-	"fmt"
 
 	"github.com/owncloud/ocis/ocis-pkg/config"
 	"github.com/owncloud/ocis/ocis-pkg/config/envdecode"
@@ -99,15 +98,15 @@ func EnsureCommons(cfg *config.Config) {
 
 func Validate(cfg *config.Config) error {
 	if cfg.TokenManager.JWTSecret == "" {
-		return fmt.Errorf("jwt secret is not set up properly, bailing out (ocis)")
+		return shared.MissingJWTTokenError("ocis")
 	}
 
 	if cfg.TransferSecret == "" {
-		return fmt.Errorf("transfer secret is not set up properly, bailing out (ocis)")
+		return shared.MissingRevaTransferSecretError("ocis")
 	}
 
 	if cfg.MachineAuthAPIKey == "" {
-		return fmt.Errorf("machine auth api key is not set up properly, bailing out (ocis)")
+		return shared.MissingMachineAuthApiKeyError("ocis")
 	}
 
 	return nil
diff --git a/ocis-pkg/shared/errors.go b/ocis-pkg/shared/errors.go
new file mode 100644
index 000000000..899def912
--- /dev/null
+++ b/ocis-pkg/shared/errors.go
@@ -0,0 +1,28 @@
+package shared
+
+import (
+	"fmt"
+
+	"github.com/owncloud/ocis/ocis-pkg/config/defaults"
+)
+
+func MissingMachineAuthApiKeyError(service string) error {
+	return fmt.Errorf("machine_auth_api_key has not your config for %s. "+
+		"Make sure your %s config contains the proper values "+
+		"(e.g. by running ocis init or setting OCIS_MACHINE_AUTH_API_KEY).\n",
+		service, defaults.BaseConfigPath())
+}
+
+func MissingJWTTokenError(service string) error {
+	return fmt.Errorf("jwt_secret has not been set properly in your config for %s. "+
+		"Make sure your %s config contains the proper values "+
+		"(e.g. by running ocis init or setting OCIS_JWT_SECRET).\n",
+		service, defaults.BaseConfigPath())
+}
+
+func MissingRevaTransferSecretError(service string) error {
+	return fmt.Errorf("transfer_secret has not been set properly in your config for %s. "+
+		"Make sure your %s config contains the proper values "+
+		"(e.g. by running ocis init or setting STORAGE_TRANSFER_SECRET).\n",
+		service, defaults.BaseConfigPath())
+}
diff --git a/ocis/pkg/command/init.go b/ocis/pkg/command/init.go
index 24d82821a..27f50b03a 100644
--- a/ocis/pkg/command/init.go
+++ b/ocis/pkg/command/init.go
@@ -41,11 +41,11 @@ func InitCommand(cfg *config.Config) *cli.Command {
 			insecureFlag := c.String("insecure")
 			insecure := false
 			if insecureFlag == "ask" {
-				answer := strings.ToLower(stringPrompt("Insecure Backends? [Yes|No]"))
+				answer := strings.ToLower(stringPrompt("Do want to configure oCIS with certificate checking disabled?\n This is not recommended for public instances! [yes | no = default]"))
 				if answer == "yes" || answer == "y" {
 					insecure = true
 				}
-			} else if insecureFlag == "true" {
+			} else if insecureFlag == strings.ToLower("true") || insecureFlag == strings.ToLower("yes") || insecureFlag == strings.ToLower("y") {
 				insecure = true
 			}
 			err := ocisinit.CreateConfig(insecure, c.Bool("force-overwrite"), c.String("config-path"))