diff --git a/apps/helpers.py b/apps/helpers.py
index 0f212b15..2b742be6 100644
--- a/apps/helpers.py
+++ b/apps/helpers.py
@@ -2,7 +2,8 @@
 from enum import Enum
 from typing import Optional
 
-from django.core.exceptions import ObjectDoesNotExist
+import regex as re
+from django.core.exceptions import ObjectDoesNotExist, ValidationError
 from django.db import transaction
 
 from apps.types_.subdomain import SubdomainCandidateName, SubdomainTuple
@@ -371,3 +372,25 @@ def save_instance_and_related_data(instance, form):
     instance.set_k8s_values()
     instance.url = get_URI(instance)
     instance.save(update_fields=["k8s_values", "url"])
+
+
+def validate_path_k8s_label_compatible(candidate: str) -> None:
+    """
+    Validates to be compatible with k8s labels specification.
+    See: https://kubernetes.io/docs/concepts/overview/working-with-objects/labels/#syntax-and-character-set
+    The RegexValidator will raise a ValidationError if the input does not match the regular expression.
+    It is up to the caller to handle the raised exception if desired.
+    """
+    error_message = (
+        "Please provide a valid path. "
+        "It can be empty. "
+        "Otherwise, it must be 63 characters or less. "
+        " It must begin and end with an alphanumeric character (a-z, or 0-9, or A-Z)."
+        " It could contain dashes ( - ), underscores ( _ ), dots ( . ), "
+        "and alphanumerics."
+    )
+
+    pattern = r"^(?:[a-zA-Z0-9](?:[a-zA-Z0-9._-]{0,61}[a-zA-Z0-9])?)?$"
+
+    if not re.match(pattern, candidate):
+        raise ValidationError(error_message)
diff --git a/apps/migrations/0019_alter_shinyinstance_shiny_site_dir.py b/apps/migrations/0019_alter_shinyinstance_shiny_site_dir.py
new file mode 100644
index 00000000..96eeb0e1
--- /dev/null
+++ b/apps/migrations/0019_alter_shinyinstance_shiny_site_dir.py
@@ -0,0 +1,20 @@
+# Generated by Django 5.1.1 on 2024-11-27 12:47
+
+import apps.models.app_types.shiny
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+    dependencies = [
+        ("apps", "0018_customappinstance_default_url_subpath"),
+    ]
+
+    operations = [
+        migrations.AlterField(
+            model_name="shinyinstance",
+            name="shiny_site_dir",
+            field=models.CharField(
+                blank=True, default="", max_length=255, validators=[apps.helpers.validate_path_k8s_label_compatible]
+            ),
+        ),
+    ]
diff --git a/apps/models/app_types/shiny.py b/apps/models/app_types/shiny.py
index f17a8080..d311e354 100644
--- a/apps/models/app_types/shiny.py
+++ b/apps/models/app_types/shiny.py
@@ -1,5 +1,6 @@
 from django.db import models
 
+from apps.helpers import validate_path_k8s_label_compatible
 from apps.models import (
     AppInstanceManager,
     BaseAppInstance,
@@ -35,7 +36,9 @@ class ShinyInstance(BaseAppInstance, SocialMixin, LogsEnabledMixin):
     container_waittime = models.IntegerField(default=20000)
     heartbeat_timeout = models.IntegerField(default=60000)
     heartbeat_rate = models.IntegerField(default=10000)
-    shiny_site_dir = models.CharField(max_length=255, default="", blank=True)
+    shiny_site_dir = models.CharField(
+        validators=[validate_path_k8s_label_compatible], max_length=255, default="", blank=True
+    )
 
     # The following three settings control the pre-init and seats behaviour (see documentation)
     # These settings override the Helm chart default values
diff --git a/apps/tests/test_forms.py b/apps/tests/test_forms.py
index 845b44d1..17d88374 100644
--- a/apps/tests/test_forms.py
+++ b/apps/tests/test_forms.py
@@ -5,6 +5,7 @@
 from django.test import TestCase
 
 from apps.forms import CustomAppForm
+from apps.helpers import validate_path_k8s_label_compatible
 from apps.models import Apps, AppStatus, Subdomain, VolumeInstance
 from apps.models.app_types.custom.custom import validate_default_url_subpath
 from projects.models import Flavor, Project
@@ -240,3 +241,71 @@ def test_invalid_default_url_subpath(invalid_default_url_subpath):
         valid_check = False
 
     assert not valid_check
+
+
+invalid_shiny_site_dir_list = [
+    "-invalidStart",  # Starts with a non-alphanumeric character
+    "invalidEnd-",  # Ends with a non-alphanumeric character
+    ".dotStart",  # Starts with a dot
+    "dotEnd.",  # Ends with a dot
+    "_underscoreStart",  # Starts with an underscore
+    "underscoreEnd_",  # Ends with an underscore
+    "label with spaces",  # Contains spaces
+    "label@value",  # Contains an invalid character (@)
+    "too_long_label_with_more_than_sixty_three_characters__1234567890",  # Exceeds 63 characters
+    "just-dashes-",  # Ends with a dash
+    "123#",  # Contains an invalid character (#)
+    ".....",  # Only contains dots
+    "-a",  # Starts with a dash
+    "_a_",  # Starts and ends with underscores
+    " ",  # Contains only whitespace
+]
+
+valid_shiny_site_dir_list = [
+    "",  # Empty string is allowed
+    "a",  # Single alphanumeric character
+    "validLabel",  # Alphanumeric characters only
+    "label-123",  # Contains a dash
+    "label_with_underscores",  # Contains underscores
+    "label.with.dots",  # Contains dots
+    "abc-def_ghi.jkl",  # Contains all allowed special characters
+    "label1",  # Ends with a number
+    "1stLabel",  # Starts with a number
+    "example-label",  # Simple example with a dash
+    "nested.label.value",  # Dots between words
+    "underscore_ending_label",  # Underscore in the middle
+    "valid-value-0123",  # Contains numbers and special characters
+    "long-valid-label-abcdefg-hijklmn-opqrstuv-wxyz",  # Long but within 63 characters
+    "labelvalue123456789",  # Combination of letters and numbers
+    "consecutive-dashes--allowed",  # Contains consecutive dashes
+    "consecutive_underscores__allowed",  # Contains consecutive underscores
+    "dots..in..between",  # Contains consecutive dots
+    "mixed__--..label",  # Contains a mix of consecutive allowed characters
+    "label---with---many---dashes",  # Multiple consecutive dashes in different parts
+    "label..with..dots",  # Multiple consecutive dots in between
+    "valid_--..mix_12",  # Combination of numbers, letters, and allowed characters
+    "simple.label-value_1-2-3",  # Mixed with numbers, dots, underscores, and dashes
+    "complex__label..value--mixed",  # A complex mix with all allowed characters in a consecutive manner
+]
+
+
+@pytest.mark.parametrize("valid_shiny_site_dir", valid_shiny_site_dir_list)
+def test_valid_shiny_site_dir(valid_shiny_site_dir):
+    valid_check = True
+    try:
+        validate_path_k8s_label_compatible(valid_shiny_site_dir)
+    except ValidationError:
+        valid_check = False
+
+    assert valid_check
+
+
+@pytest.mark.parametrize("invalid_shiny_site_dir", invalid_shiny_site_dir_list)
+def test_invalid_shiny_site_dir(invalid_shiny_site_dir):
+    valid_check = True
+    try:
+        validate_path_k8s_label_compatible(invalid_shiny_site_dir)
+    except ValidationError:
+        valid_check = False
+
+    assert not valid_check
diff --git a/cypress/e2e/ui-tests/test-deploy-app.cy.js b/cypress/e2e/ui-tests/test-deploy-app.cy.js
index cc82ca63..4cffdff7 100644
--- a/cypress/e2e/ui-tests/test-deploy-app.cy.js
+++ b/cypress/e2e/ui-tests/test-deploy-app.cy.js
@@ -278,6 +278,7 @@ describe("Test deploying app", () => {
     })
 
     // This test is skipped because it will only work against a Serve instance running on our cluster. should be switched on for the e2e tests against remote.
+    // We need to add a test here for validating Site-dir option. See SS-1206 for details
     it.skip("can deploy a shiny app", { defaultCommandTimeout: defaultCmdTimeoutMs }, () => {
         // Names of objects to create
         const project_name = "e2e-deploy-app-test"