diff --git a/source/client-side-encryption/etc/data/encryptedFields-prefix-suffix-ci-di.json b/source/client-side-encryption/etc/data/encryptedFields-prefix-suffix-ci-di.json
new file mode 100644
index 0000000000..c43bf9390d
--- /dev/null
+++ b/source/client-side-encryption/etc/data/encryptedFields-prefix-suffix-ci-di.json
@@ -0,0 +1,40 @@
+{
+  "fields": [
+    {
+      "keyId": {
+        "$binary": {
+          "base64": "EjRWeBI0mHYSNBI0VniQEg==",
+          "subType": "04"
+        }
+      },
+      "path": "encryptedText",
+      "bsonType": "string",
+      "queries": [
+        {
+          "queryType": "prefixPreview",
+          "strMinQueryLength": {
+            "$numberInt": "2"
+          },
+          "strMaxQueryLength": {
+            "$numberInt": "10"
+          },
+          "contention": 0,
+          "caseSensitive": false,
+          "diacriticSensitive": false
+        },
+        {
+          "queryType": "suffixPreview",
+          "strMinQueryLength": {
+            "$numberInt": "2"
+          },
+          "strMaxQueryLength": {
+            "$numberInt": "10"
+          },
+          "contention": 0,
+          "caseSensitive": false,
+          "diacriticSensitive": false
+        }
+      ]
+    }
+  ]
+}
diff --git a/source/client-side-encryption/tests/README.md b/source/client-side-encryption/tests/README.md
index 2b6d7b9933..624d920ffa 100644
--- a/source/client-side-encryption/tests/README.md
+++ b/source/client-side-encryption/tests/README.md
@@ -3886,6 +3886,9 @@ create the following collections with majority write concern:
 - `db.prefix-suffix` using the `encryptedFields` option set to the contents of
     [encryptedFields-prefix-suffix.json](https://github.com/mongodb/specifications/tree/master/source/client-side-encryption/etc/data/encryptedFields-prefix-suffix.json).
     Skip this step if testing server 9.0.0+.
+- `db.prefix-suffix-ci-di` using the `encryptedFields` option set to the contents of
+    [encryptedFields-prefix-suffix-ci-di.json](https://github.com/mongodb/specifications/tree/master/source/client-side-encryption/etc/data/encryptedFields-prefix-suffix-ci-di.json).
+    Skip this step if testing server 9.0.0+.
 - `db.substring` using the `encryptedFields` option set to the contents of
     [encryptedFields-substring.json](https://github.com/mongodb/specifications/tree/master/source/client-side-encryption/etc/data/encryptedFields-substring.json)
 
@@ -3921,6 +3924,22 @@ class AutoEncryptionOpts {
 }
 ```
 
+Create a MongoClient with auto-encryption enabled (without `bypassQueryAnalysis`) using these `AutoEncryptionOpts`:
+
+```typescript
+class AutoEncryptionOpts {
+   keyVaultNamespace: "keyvault.datakeys",
+   kmsProviders: { "local": { "key": <base64 decoding of LOCAL_MASTERKEY> } },
+}
+```
+
+Use that client to insert the following document into `db.prefix-suffix-ci-di` with majority write concern. Skip this
+step if testing server 9.0.0+.
+
+```javascript
+{ "encryptedText": "BingQiLin" }
+```
+
 Use `clientEncryption` to encrypt the string `"foobarbaz"` with the following `EncryptOpts`:
 
 ```typescript
@@ -4194,3 +4213,268 @@ class EncryptOpts {
 
 Expect an error from libmongocrypt with a message containing the string: "contention factor is required for textPreview
 algorithm".
+
+#### Case 8: can find a case and diacritic-insensitively indexed document by prefix and suffix
+
+`"BingQiLin"` was inserted via auto-encryption in Test Setup, indexed under the
+`caseSensitive: false, diacriticSensitive: false` prefix configuration and the
+`caseSensitive: false, diacriticSensitive: false` suffix configuration of `db.prefix-suffix-ci-di`.
+
+Use `clientEncryption.encrypt()` to encrypt the string `"bing"` with the following `EncryptOpts`:
+
+```typescript
+class EncryptOpts {
+   keyId : <key1ID>,
+   algorithm: "TextPreview",
+   queryType: "prefix",
+   contentionFactor: 0,
+   textOpts: TextOpts {
+      caseSensitive: false,
+      diacriticSensitive: false,
+      prefix: PrefixOpts {
+        strMaxQueryLength: 10,
+        strMinQueryLength: 2,
+     }
+   },
+}
+```
+
+Use `encryptedClient` to run a "find" operation on the `db.prefix-suffix-ci-di` collection with the following filter:
+
+```javascript
+{ $expr: { $encStrStartsWith: {input: '$encryptedText', prefix: <encrypted 'bing'>} } }
+```
+
+Assert the following document is returned:
+
+```javascript
+{ "encryptedText": "BingQiLin" }
+```
+
+Use `clientEncryption.encrypt()` to encrypt the string `"lin"` with the following `EncryptOpts`:
+
+```typescript
+class EncryptOpts {
+   keyId : <key1ID>,
+   algorithm: "TextPreview",
+   queryType: "suffix",
+   contentionFactor: 0,
+   textOpts: TextOpts {
+      caseSensitive: false,
+      diacriticSensitive: true,
+      suffix: SuffixOpts {
+        strMaxQueryLength: 10,
+        strMinQueryLength: 2,
+     }
+   },
+}
+```
+
+Use `encryptedClient` to run a "find" operation on the `db.prefix-suffix-ci-di` collection with the following filter:
+
+```javascript
+{ $expr: { $encStrEndsWith: {input: '$encryptedText', suffix: <encrypted 'lin'>} } }
+```
+
+Assert the following document is returned:
+
+```javascript
+{ "encryptedText": "BingQiLin" }
+```
+
+#### Case 9: can find a diacritic-insensitively indexed document by prefix and suffix
+
+Create a MongoClient with auto-encryption enabled (without `bypassQueryAnalysis`) using these `AutoEncryptionOpts`:
+
+```typescript
+class AutoEncryptionOpts {
+   keyVaultNamespace: "keyvault.datakeys",
+   kmsProviders: { "local": { "key": <base64 decoding of LOCAL_MASTERKEY> } },
+}
+```
+
+Use that client to insert the following document into `db.prefix-suffix-ci-di` with majority write concern:
+
+```javascript
+{ "encryptedText": "cafébarbäz" }
+```
+
+Use `clientEncryption.encrypt()` to encrypt the string `"cafe"` with the following `EncryptOpts`:
+
+```typescript
+class EncryptOpts {
+   keyId : <key1ID>,
+   algorithm: "TextPreview",
+   queryType: "prefix",
+   contentionFactor: 0,
+   textOpts: TextOpts {
+      caseSensitive: true,
+      diacriticSensitive: false,
+      prefix: PrefixOpts {
+        strMaxQueryLength: 10,
+        strMinQueryLength: 2,
+     }
+   },
+}
+```
+
+Use `encryptedClient` to run a "find" operation on the `db.prefix-suffix-ci-di` collection with the following filter:
+
+```javascript
+{ $expr: { $encStrStartsWith: {input: '$encryptedText', prefix: <encrypted 'cafe'>} } }
+```
+
+Assert the following document is returned:
+
+```javascript
+{ "encryptedText": "cafébarbäz" }
+```
+
+Use `clientEncryption.encrypt()` to encrypt the string `"baz"` with the following `EncryptOpts`:
+
+```typescript
+class EncryptOpts {
+   keyId : <key1ID>,
+   algorithm: "TextPreview",
+   queryType: "suffix",
+   contentionFactor: 0,
+   textOpts: TextOpts {
+      caseSensitive: true,
+      diacriticSensitive: false,
+      suffix: SuffixOpts {
+        strMaxQueryLength: 10,
+        strMinQueryLength: 2,
+     }
+   },
+}
+```
+
+Use `encryptedClient` to run a "find" operation on the `db.prefix-suffix-ci-di` collection with the following filter:
+
+```javascript
+{ $expr: { $encStrEndsWith: {input: '$encryptedText', suffix: <encrypted 'baz'>} } }
+```
+
+Assert the following document is returned:
+
+```javascript
+{ "encryptedText": "cafébarbäz" }
+```
+
+#### Case 10: can find a case-insensitively indexed document by substring
+
+Use `clientEncryption.encrypt()` to encrypt the string `"FooBarBaz"` with the following `EncryptOpts`:
+
+```typescript
+class EncryptOpts {
+   keyId : <key1ID>,
+   algorithm: "TextPreview",
+   contentionFactor: 0,
+   textOpts: TextOpts {
+      caseSensitive: false,
+      diacriticSensitive: true,
+      substring: SubstringOpts {
+        strMaxLength: 10,
+        strMaxQueryLength: 10,
+        strMinQueryLength: 2,
+      },
+   },
+}
+```
+
+Use `encryptedClient` to insert the following document into `db.substring` with majority write concern:
+
+```javascript
+{ "encryptedText": <encrypted 'FooBarBaz'> }
+```
+
+Use `clientEncryption.encrypt()` to encrypt the string `"bar"` with the following `EncryptOpts`:
+
+```typescript
+class EncryptOpts {
+   keyId : <key1ID>,
+   algorithm: "TextPreview",
+   queryType: "substring",
+   contentionFactor: 0,
+   textOpts: TextOpts {
+      caseSensitive: false,
+      diacriticSensitive: true,
+      substring: SubstringOpts {
+        strMaxLength: 10,
+        strMaxQueryLength: 10,
+        strMinQueryLength: 2,
+      }
+   },
+}
+```
+
+Use `encryptedClient` to run a "find" operation on the `db.substring` collection with the following filter:
+
+```javascript
+{ $expr: { $encStrContains: {input: '$encryptedText', substring: <encrypted 'bar'>} } }
+```
+
+Assert the following document is returned:
+
+```javascript
+{ "encryptedText": "FooBarBaz" }
+```
+
+#### Case 11: can find a diacritic-insensitively indexed document by substring
+
+Use `clientEncryption.encrypt()` to encrypt the string `"foocafébaz"` with the following `EncryptOpts`:
+
+```typescript
+class EncryptOpts {
+   keyId : <key1ID>,
+   algorithm: "TextPreview",
+   contentionFactor: 0,
+   textOpts: TextOpts {
+      caseSensitive: true,
+      diacriticSensitive: false,
+      substring: SubstringOpts {
+        strMaxLength: 10,
+        strMaxQueryLength: 10,
+        strMinQueryLength: 2,
+      },
+   },
+}
+```
+
+Use `encryptedClient` to insert the following document into `db.substring` with majority write concern:
+
+```javascript
+{ "encryptedText": <encrypted 'foocafébaz'> }
+```
+
+Use `clientEncryption.encrypt()` to encrypt the string `"cafe"` with the following `EncryptOpts`:
+
+```typescript
+class EncryptOpts {
+   keyId : <key1ID>,
+   algorithm: "TextPreview",
+   queryType: "substring",
+   contentionFactor: 0,
+   textOpts: TextOpts {
+      caseSensitive: true,
+      diacriticSensitive: false,
+      substring: SubstringOpts {
+        strMaxLength: 10,
+        strMaxQueryLength: 10,
+        strMinQueryLength: 2,
+      }
+   },
+}
+```
+
+Use `encryptedClient` to run a "find" operation on the `db.substring` collection with the following filter:
+
+```javascript
+{ $expr: { $encStrContains: {input: '$encryptedText', substring: <encrypted 'cafe'>} } }
+```
+
+Assert the following document is returned:
+
+```javascript
+{ "encryptedText": "foocafébaz" }
+```