diff --git a/src/Api/Models/Public/Request/OrganizationImportRequestModel.cs b/src/Api/Models/Public/Request/OrganizationImportRequestModel.cs
index 285d4475d5..ffdb3ebc25 100644
--- a/src/Api/Models/Public/Request/OrganizationImportRequestModel.cs
+++ b/src/Api/Models/Public/Request/OrganizationImportRequestModel.cs
@@ -1,8 +1,10 @@
 using System;
 using System.Collections.Generic;
 using System.ComponentModel.DataAnnotations;
+using System.Text.Json.Serialization;
 using Bit.Core.Entities;
 using Bit.Core.Models.Business;
+using Bit.Core.Utilities;
 
 namespace Bit.Api.Models.Public.Request
 {
@@ -41,10 +43,12 @@ namespace Bit.Api.Models.Public.Request
             /// <example>external_id_123456</example>
             [Required]
             [StringLength(300)]
+            [JsonConverter(typeof(PermissiveStringConverter))]
             public string ExternalId { get; set; }
             /// <summary>
             /// The associated external ids for members in this group.
             /// </summary>
+            [JsonConverter(typeof(PermissiveStringEnumerableConverter))]
             public IEnumerable<string> MemberExternalIds { get; set; }
 
             public ImportedGroup ToImportedGroup(Guid organizationId)
@@ -79,6 +83,7 @@ namespace Bit.Api.Models.Public.Request
             /// <example>external_id_123456</example>
             [Required]
             [StringLength(300)]
+            [JsonConverter(typeof(PermissiveStringConverter))]
             public string ExternalId { get; set; }
             /// <summary>
             /// Determines if this member should be removed from the organization during import.
diff --git a/src/Core/Utilities/JsonHelpers.cs b/src/Core/Utilities/JsonHelpers.cs
index 6cb54676cd..954a9a14d5 100644
--- a/src/Core/Utilities/JsonHelpers.cs
+++ b/src/Core/Utilities/JsonHelpers.cs
@@ -1,4 +1,7 @@
 using System;
+using System.Collections.Generic;
+using System.Diagnostics;
+using System.Linq;
 using System.Text.Json;
 using System.Text.Json.Serialization;
 using NS = Newtonsoft.Json;
@@ -129,4 +132,72 @@ namespace Bit.Core.Utilities
             writer.WriteStringValue(CoreHelpers.ToEpocMilliseconds(value.Value).ToString());
         }
     }
+
+    /// <summary>
+    /// Allows reading a string from a JSON number or string, should only be used on <see cref="string" /> properties
+    /// </summary>
+    public class PermissiveStringConverter : JsonConverter<string>
+    {
+        internal static PermissiveStringConverter Instance = new();
+
+        public override string Read(ref Utf8JsonReader reader, Type typeToConvert, JsonSerializerOptions options)
+        {
+            return reader.TokenType switch
+            {
+                JsonTokenType.String => reader.GetString(),
+                JsonTokenType.Number => reader.GetDecimal().ToString(),
+                JsonTokenType.True => bool.TrueString,
+                JsonTokenType.False => bool.FalseString,
+                _ => throw new JsonException($"Unsupported TokenType: {reader.TokenType}"),
+            };
+        }
+
+        public override void Write(Utf8JsonWriter writer, string value, JsonSerializerOptions options)
+        {
+            writer.WriteStringValue(value);
+        }
+    }
+
+    /// <summary>
+    /// Allows reading a JSON array of number or string, should only be used on <see cref="IEnumerable{T}" /> whose generic type is <see cref="string" />
+    /// </summary>
+    public class PermissiveStringEnumerableConverter : JsonConverter<IEnumerable<string>>
+    {
+        public override IEnumerable<string> Read(ref Utf8JsonReader reader, Type typeToConvert, JsonSerializerOptions options)
+        {
+            var stringList = new List<string>();
+
+            // Handle special cases or throw
+            if (reader.TokenType != JsonTokenType.StartArray)
+            {
+                // An array was expected but to be extra permissive allow reading from anything other than an object
+                if (reader.TokenType == JsonTokenType.StartObject)
+                {
+                    throw new JsonException("Cannot read JSON Object to an IEnumerable<string>.");
+                }
+
+                stringList.Add(PermissiveStringConverter.Instance.Read(ref reader, typeof(string), options));
+                return stringList;
+            }
+
+            while (reader.Read() && reader.TokenType != JsonTokenType.EndArray)
+            {
+                stringList.Add(PermissiveStringConverter.Instance.Read(ref reader, typeof(string), options));
+            }
+
+            return stringList;
+        }
+
+        public override void Write(Utf8JsonWriter writer, IEnumerable<string> value, JsonSerializerOptions options)
+        {
+            writer.WriteStartArray();
+
+            foreach (var str in value)
+            {
+                PermissiveStringConverter.Instance.Write(writer, str, options);
+            }
+
+            writer.WriteEndArray();
+        }
+    }
 }
diff --git a/test/Core.Test/Utilities/PermissiveStringConverterTests.cs b/test/Core.Test/Utilities/PermissiveStringConverterTests.cs
new file mode 100644
index 0000000000..36945bbd19
--- /dev/null
+++ b/test/Core.Test/Utilities/PermissiveStringConverterTests.cs
@@ -0,0 +1,159 @@
+using System.Collections.Generic;
+using System.Linq;
+using System.Text.Json;
+using System.Text.Json.Serialization;
+using Bit.Core.Utilities;
+using Bit.Test.Common.Helpers;
+using Xunit;
+
+namespace Bit.Core.Test.Utilities
+{
+    public class PermissiveStringConverterTests
+    {
+        private const string numberJson = "{ \"StringProp\": 1, \"EnumerableStringProp\": [ 2, 3 ]}";
+        private const string stringJson = "{ \"StringProp\": \"1\", \"EnumerableStringProp\": [ \"2\", \"3\" ]}";
+        private const string nullAndEmptyJson = "{ \"StringProp\": null, \"EnumerableStringProp\": [] }";
+        private const string singleValueJson = "{ \"StringProp\": 1, \"EnumerableStringProp\": \"Hello!\" }";
+        private const string nullJson = "{ \"StringProp\": null, \"EnumerableStringProp\": null }";
+        private const string boolJson = "{ \"StringProp\": true, \"EnumerableStringProp\": [ false, 1.2]}";
+        private const string objectJsonOne = "{ \"StringProp\": { \"Message\": \"Hi\"}, \"EnumerableStringProp\": []}";
+        private const string objectJsonTwo = "{ \"StringProp\": \"Hi\", \"EnumerableStringProp\": {}}";
+        private readonly string bigNumbersJson =
+        "{ \"StringProp\":" + decimal.MinValue + ", \"EnumerableStringProp\": [" + ulong.MaxValue + ", " + long.MinValue + "]}";
+
+        [Theory]
+        [InlineData(numberJson)]
+        [InlineData(stringJson)]
+        public void Read_Success(string json)
+        {
+            var obj = JsonSerializer.Deserialize<TestObject>(json);
+            Assert.Equal("1", obj.StringProp);
+            Assert.Equal(2, obj.EnumerableStringProp.Count());
+            Assert.Equal("2", obj.EnumerableStringProp.ElementAt(0));
+            Assert.Equal("3", obj.EnumerableStringProp.ElementAt(1));
+        }
+
+        [Fact]
+        public void Read_Boolean_Success()
+        {
+            var obj = JsonSerializer.Deserialize<TestObject>(boolJson);
+            Assert.Equal("True", obj.StringProp);
+            Assert.Equal(2, obj.EnumerableStringProp.Count());
+            Assert.Equal("False", obj.EnumerableStringProp.ElementAt(0));
+            Assert.Equal("1.2", obj.EnumerableStringProp.ElementAt(1));
+        }
+
+        [Fact]
+        public void Read_BigNumbers_Success()
+        {
+            var obj = JsonSerializer.Deserialize<TestObject>(bigNumbersJson);
+            Assert.Equal(decimal.MinValue.ToString(), obj.StringProp);
+            Assert.Equal(2, obj.EnumerableStringProp.Count());
+            Assert.Equal(ulong.MaxValue.ToString(), obj.EnumerableStringProp.ElementAt(0));
+            Assert.Equal(long.MinValue.ToString(), obj.EnumerableStringProp.ElementAt(1));
+        }
+
+        [Fact]
+        public void Read_SingleValue_Success()
+        {
+            var obj = JsonSerializer.Deserialize<TestObject>(singleValueJson);
+            Assert.Equal("1", obj.StringProp);
+            Assert.Single(obj.EnumerableStringProp);
+            Assert.Equal("Hello!", obj.EnumerableStringProp.ElementAt(0));
+        }
+
+        [Fact]
+        public void Read_NullAndEmptyJson_Success()
+        {
+            var obj = JsonSerializer.Deserialize<TestObject>(nullAndEmptyJson);
+            Assert.Null(obj.StringProp);
+            Assert.Empty(obj.EnumerableStringProp);
+        }
+
+        [Fact]
+        public void Read_Null_Success()
+        {
+            var obj = JsonSerializer.Deserialize<TestObject>(nullJson);
+            Assert.Null(obj.StringProp);
+            Assert.Null(obj.EnumerableStringProp);
+        }
+
+        [Theory]
+        [InlineData(objectJsonOne)]
+        [InlineData(objectJsonTwo)]
+        public void Read_Object_Throws(string json)
+        {
+            var exception = Assert.Throws<JsonException>(() => JsonSerializer.Deserialize<TestObject>(json));
+        }
+
+        [Fact]
+        public void Write_Success()
+        {
+            var json = JsonSerializer.Serialize(new TestObject
+            {
+                StringProp = "1",
+                EnumerableStringProp = new List<string>
+                {
+                    "2",
+                    "3",
+                },
+            });
+
+            var jsonElement = JsonDocument.Parse(json).RootElement;
+
+            var stringProp = AssertHelper.AssertJsonProperty(jsonElement, "StringProp", JsonValueKind.String);
+            Assert.Equal("1", stringProp.GetString());
+            var list = AssertHelper.AssertJsonProperty(jsonElement, "EnumerableStringProp", JsonValueKind.Array);
+            Assert.Equal(2, list.GetArrayLength());
+            var firstElement = list[0];
+            Assert.Equal(JsonValueKind.String, firstElement.ValueKind);
+            Assert.Equal("2", firstElement.GetString());
+            var secondElement = list[1];
+            Assert.Equal(JsonValueKind.String, secondElement.ValueKind);
+            Assert.Equal("3", secondElement.GetString());
+        }
+
+        [Fact]
+        public void Write_Null()
+        {
+            // When the values are null the converters aren't actually ran and it automatically serializes null
+            var json = JsonSerializer.Serialize(new TestObject
+            {
+                StringProp = null,
+                EnumerableStringProp = null,
+            });
+
+            var jsonElement = JsonDocument.Parse(json).RootElement;
+
+            AssertHelper.AssertJsonProperty(jsonElement, "StringProp", JsonValueKind.Null);
+            AssertHelper.AssertJsonProperty(jsonElement, "EnumerableStringProp", JsonValueKind.Null);
+        }
+
+        [Fact]
+        public void Write_Empty()
+        {
+            // When the values are null the converters aren't actually ran and it automatically serializes null
+            var json = JsonSerializer.Serialize(new TestObject
+            {
+                StringProp = "",
+                EnumerableStringProp = Enumerable.Empty<string>(),
+            });
+
+            var jsonElement = JsonDocument.Parse(json).RootElement;
+
+            var stringVal = AssertHelper.AssertJsonProperty(jsonElement, "StringProp", JsonValueKind.String).GetString();
+            Assert.Equal("", stringVal);
+            var array = AssertHelper.AssertJsonProperty(jsonElement, "EnumerableStringProp", JsonValueKind.Array);
+            Assert.Equal(0, array.GetArrayLength());
+        }
+    }
+
+    public class TestObject
+    {
+        [JsonConverter(typeof(PermissiveStringConverter))]
+        public string StringProp { get; set; }
+
+        [JsonConverter(typeof(PermissiveStringEnumerableConverter))]
+        public IEnumerable<string> EnumerableStringProp { get; set; }
+    }
+}