diff --git a/.evergreen/config.yml b/.evergreen/config.yml
index 90da768350..bf51417028 100644
--- a/.evergreen/config.yml
+++ b/.evergreen/config.yml
@@ -553,6 +553,25 @@ functions:
           KMS_MOCK_SERVERS_RUNNING: "true"
         args: [*task-runner, evg-test-kmip]
 
+  run-retry-kms-requests:
+    - command: subprocess.exec
+      type: test
+      params:
+        binary: "bash"
+        env: 
+          GO_BUILD_TAGS: cse
+        include_expansions_in_env: [AUTH, SSL, MONGODB_URI, TOPOLOGY, 
+          MONGO_GO_DRIVER_COMPRESSOR]
+        args: [*task-runner, setup-test]
+    - command: subprocess.exec
+      type: test
+      params:
+        binary: "bash"
+        env:
+          KMS_FAILPOINT_CA_FILE: "${DRIVERS_TOOLS}/.evergreen/x509gen/ca.pem"
+          KMS_FAILPOINT_SERVER_RUNNING: "true"
+        args: [*task-runner, evg-test-retry-kms-requests]
+
   run-fuzz-tests:
     - command: subprocess.exec
       type: test
@@ -1440,7 +1459,7 @@ tasks:
           SSL: "nossl"
 
   - name: "test-kms-tls-invalid-cert"
-    tags: ["kms-tls"]
+    tags: ["kms-test"]
     commands:
       - func: bootstrap-mongo-orchestration
         vars:
@@ -1456,7 +1475,7 @@ tasks:
           SSL: "nossl"
 
   - name: "test-kms-tls-invalid-hostname"
-    tags: ["kms-tls"]
+    tags: ["kms-test"]
     commands:
       - func: bootstrap-mongo-orchestration
         vars:
@@ -1486,6 +1505,17 @@ tasks:
           AUTH: "noauth"
           SSL: "nossl"
 
+  - name: "test-retry-kms-requests"
+    tags: ["kms-test"]
+    commands:
+      - func: bootstrap-mongo-orchestration
+        vars:
+          TOPOLOGY: "server"
+          AUTH: "noauth"
+          SSL: "nossl"
+      - func: start-cse-servers
+      - func: run-retry-kms-requests
+
   - name: "test-serverless"
     tags: ["serverless"]
     commands:
@@ -2163,11 +2193,11 @@ buildvariants:
     tasks:
       - name: ".versioned-api"
 
-  - matrix_name: "kms-tls-test"
+  - matrix_name: "kms-test"
     matrix_spec: { version: ["7.0"], os-ssl-40: ["rhel87-64"] }
-    display_name: "KMS TLS ${os-ssl-40}"
+    display_name: "KMS TEST ${os-ssl-40}"
     tasks:
-      - name: ".kms-tls"
+      - name: ".kms-test"
 
   - matrix_name: "load-balancer-test"
     tags: ["pullrequest"]
diff --git a/Taskfile.yml b/Taskfile.yml
index f22427a640..d93a7e4e9b 100644
--- a/Taskfile.yml
+++ b/Taskfile.yml
@@ -141,6 +141,9 @@ tasks:
   evg-test-kms:
     - go test -exec "env PKG_CONFIG_PATH=${PKG_CONFIG_PATH} LD_LIBRARY_PATH=${LD_LIBRARY_PATH}" ${BUILD_TAGS} -v -timeout {{.TEST_TIMEOUT}}s ./internal/integration -run TestClientSideEncryptionProse/kms_tls_tests >> test.suite
 
+  evg-test-retry-kms-requests:
+    - go test -exec "env PKG_CONFIG_PATH=${PKG_CONFIG_PATH} LD_LIBRARY_PATH=${LD_LIBRARY_PATH}" ${BUILD_TAGS} -v -timeout {{.TEST_TIMEOUT}}s ./internal/integration -run TestClientSideEncryptionProse/kms_retry_tests >> test.suite
+
   evg-test-load-balancers:
     # Load balancer should be tested with all unified tests as well as tests in the following
     # components: retryable reads, retryable writes, change streams, initial DNS seedlist discovery.
diff --git a/etc/install-libmongocrypt.sh b/etc/install-libmongocrypt.sh
index 646721a8f7..a94d648eae 100755
--- a/etc/install-libmongocrypt.sh
+++ b/etc/install-libmongocrypt.sh
@@ -3,7 +3,7 @@
 # This script installs libmongocrypt into an "install" directory.
 set -eux
 
-LIBMONGOCRYPT_TAG="1.11.0"
+LIBMONGOCRYPT_TAG="1.12.0"
 
 # Install libmongocrypt based on OS.
 if [ "Windows_NT" = "${OS:-}" ]; then
diff --git a/internal/integration/client_side_encryption_prose_test.go b/internal/integration/client_side_encryption_prose_test.go
index 0620b9ff10..81011255f4 100644
--- a/internal/integration/client_side_encryption_prose_test.go
+++ b/internal/integration/client_side_encryption_prose_test.go
@@ -14,6 +14,7 @@ import (
 	"context"
 	"crypto/tls"
 	"encoding/base64"
+	"encoding/json"
 	"fmt"
 	"io/ioutil"
 	"net"
@@ -30,6 +31,7 @@ import (
 	"go.mongodb.org/mongo-driver/v2/internal/handshake"
 	"go.mongodb.org/mongo-driver/v2/internal/integration/mtest"
 	"go.mongodb.org/mongo-driver/v2/internal/integtest"
+	"go.mongodb.org/mongo-driver/v2/internal/require"
 	"go.mongodb.org/mongo-driver/v2/mongo"
 	"go.mongodb.org/mongo-driver/v2/mongo/options"
 	"go.mongodb.org/mongo-driver/v2/mongo/writeconcern"
@@ -2918,7 +2920,7 @@ func TestClientSideEncryptionProse(t *testing.T) {
 		}
 	})
 
-	mt.RunOpts("22. range explicit encryption applies defaults", qeRunOpts22, func(mt *mtest.T) {
+	mt.RunOpts("23. range explicit encryption applies defaults", qeRunOpts22, func(mt *mtest.T) {
 		err := mt.Client.Database("keyvault").Collection("datakeys").Drop(context.Background())
 		assert.Nil(mt, err, "error on Drop: %v", err)
 
@@ -2979,6 +2981,147 @@ func TestClientSideEncryptionProse(t *testing.T) {
 			assert.Greater(t, len(payload.Data), len(payloadDefaults.Data), "the returned payload size is expected to be greater than %d", len(payloadDefaults.Data))
 		})
 	})
+
+	mt.RunOpts("24. kms retry tests", noClientOpts, func(mt *mtest.T) {
+		kmsTlsTestcase := os.Getenv("KMS_FAILPOINT_SERVER_RUNNING")
+		if kmsTlsTestcase == "" {
+			mt.Skipf("Skipping test as KMS_FAILPOINT_SERVER_RUNNING is not set")
+		}
+
+		mt.Parallel()
+
+		tlsCAFile := os.Getenv("KMS_FAILPOINT_CA_FILE")
+		require.NotEqual(mt, tlsCAFile, "", "failed to load CA file")
+
+		clientAndCATlsMap := map[string]interface{}{
+			"tlsCAFile": tlsCAFile,
+		}
+		tlsCfg, err := options.BuildTLSConfig(clientAndCATlsMap)
+		require.NoError(mt, err, "BuildTLSConfig error: %v", err)
+
+		setFailPoint := func(failure string, count int) error {
+			url := fmt.Sprintf("https://localhost:9003/set_failpoint/%s", failure)
+			var payloadBuf bytes.Buffer
+			body := map[string]int{"count": count}
+			json.NewEncoder(&payloadBuf).Encode(body)
+			req, err := http.NewRequest(http.MethodPost, url, &payloadBuf)
+			if err != nil {
+				return err
+			}
+
+			client := &http.Client{
+				Transport: &http.Transport{TLSClientConfig: tlsCfg},
+			}
+			res, err := client.Do(req)
+			if err != nil {
+				return err
+			}
+			return res.Body.Close()
+		}
+
+		kmsProviders := map[string]map[string]interface{}{
+			"aws": {
+				"accessKeyId":     awsAccessKeyID,
+				"secretAccessKey": awsSecretAccessKey,
+			},
+			"azure": {
+				"tenantId":                 azureTenantID,
+				"clientId":                 azureClientID,
+				"clientSecret":             azureClientSecret,
+				"identityPlatformEndpoint": "127.0.0.1:9003",
+			},
+			"gcp": {
+				"email":      gcpEmail,
+				"privateKey": gcpPrivateKey,
+				"endpoint":   "127.0.0.1:9003",
+			},
+		}
+
+		dataKeys := []struct {
+			provider  string
+			masterKey interface{}
+		}{
+			{"aws", bson.D{
+				{"region", "foo"},
+				{"key", "bar"},
+				{"endpoint", "127.0.0.1:9003"},
+			}},
+			{"azure", bson.D{
+				{"keyVaultEndpoint", "127.0.0.1:9003"},
+				{"keyName", "foo"},
+			}},
+			{"gcp", bson.D{
+				{"projectId", "foo"},
+				{"location", "bar"},
+				{"keyRing", "baz"},
+				{"keyName", "qux"},
+				{"endpoint", "127.0.0.1:9003"},
+			}},
+		}
+
+		testCases := []struct {
+			name    string
+			failure string
+		}{
+			{"Case 1: createDataKey and encrypt with TCP retry", "network"},
+			{"Case 2: createDataKey and encrypt with HTTP retry", "http"},
+		}
+
+		for _, tc := range testCases {
+			for _, dataKey := range dataKeys {
+				mt.Run(fmt.Sprintf("%s_%s", tc.name, dataKey.provider), func(mt *mtest.T) {
+					keyVaultClient, err := mongo.Connect(options.Client().ApplyURI(mtest.ClusterURI()))
+					require.NoError(mt, err, "error on Connect: %v", err)
+
+					ceo := options.ClientEncryption().
+						SetKeyVaultNamespace(kvNamespace).
+						SetKmsProviders(kmsProviders).
+						SetTLSConfig(map[string]*tls.Config{dataKey.provider: tlsCfg})
+					clientEncryption, err := mongo.NewClientEncryption(keyVaultClient, ceo)
+					require.NoError(mt, err, "error on NewClientEncryption: %v", err)
+
+					err = setFailPoint(tc.failure, 1)
+					require.NoError(mt, err, "mock server error: %v", err)
+
+					dkOpts := options.DataKey().SetMasterKey(dataKey.masterKey)
+					var keyID bson.Binary
+					keyID, err = clientEncryption.CreateDataKey(context.Background(), dataKey.provider, dkOpts)
+					require.NoError(mt, err, "error in CreateDataKey: %v", err)
+
+					err = setFailPoint(tc.failure, 1)
+					require.NoError(mt, err, "mock server error: %v", err)
+
+					testVal := bson.RawValue{Type: bson.TypeInt32, Value: bsoncore.AppendInt32(nil, 123)}
+					eo := options.Encrypt().
+						SetKeyID(keyID).
+						SetAlgorithm("AEAD_AES_256_CBC_HMAC_SHA_512-Deterministic")
+					_, err = clientEncryption.Encrypt(context.Background(), testVal, eo)
+					require.NoError(mt, err, "error in Encrypt: %v", err)
+				})
+			}
+		}
+
+		for _, dataKey := range dataKeys {
+			mt.Run(fmt.Sprintf("Case 3: createDataKey fails after too many retries_%s", dataKey.provider), func(mt *mtest.T) {
+				keyVaultClient, err := mongo.Connect(options.Client().ApplyURI(mtest.ClusterURI()))
+				require.NoError(mt, err, "error on Connect: %v", err)
+
+				ceo := options.ClientEncryption().
+					SetKeyVaultNamespace(kvNamespace).
+					SetKmsProviders(kmsProviders).
+					SetTLSConfig(map[string]*tls.Config{dataKey.provider: tlsCfg})
+				clientEncryption, err := mongo.NewClientEncryption(keyVaultClient, ceo)
+				require.NoError(mt, err, "error on NewClientEncryption: %v", err)
+
+				err = setFailPoint("network", 4)
+				require.NoError(mt, err, "mock server error: %v", err)
+
+				dkOpts := options.DataKey().SetMasterKey(dataKey.masterKey)
+				_, err = clientEncryption.CreateDataKey(context.Background(), dataKey.provider, dkOpts)
+				require.ErrorContains(mt, err, "KMS request failed after 3 retries due to a network error")
+			})
+		}
+	})
 }
 
 func getWatcher(mt *mtest.T, streamType mongo.StreamType, cpt *cseProseTest) watcher {
diff --git a/x/mongo/driver/crypt.go b/x/mongo/driver/crypt.go
index 4368fd125d..7a51b7a4b9 100644
--- a/x/mongo/driver/crypt.go
+++ b/x/mongo/driver/crypt.go
@@ -9,9 +9,7 @@ package driver
 import (
 	"context"
 	"crypto/tls"
-	"errors"
 	"fmt"
-	"io"
 	"strings"
 	"time"
 
@@ -399,8 +397,8 @@ func (c *crypt) decryptKey(kmsCtx *mongocrypt.KmsContext) error {
 
 		res := make([]byte, bytesNeeded)
 		bytesRead, err := conn.Read(res)
-		if err != nil && !errors.Is(err, io.EOF) {
-			return err
+		if err != nil {
+			return kmsCtx.RequestError()
 		}
 
 		if err = kmsCtx.FeedResponse(res[:bytesRead]); err != nil {
diff --git a/x/mongo/driver/mongocrypt/mongocrypt.go b/x/mongo/driver/mongocrypt/mongocrypt.go
index 5f34f5cd71..7f7c3e8fc9 100644
--- a/x/mongo/driver/mongocrypt/mongocrypt.go
+++ b/x/mongo/driver/mongocrypt/mongocrypt.go
@@ -53,6 +53,7 @@ func NewMongoCrypt(opts *options.MongoCryptOptions) (*MongoCrypt, error) {
 	if wrapped == nil {
 		return nil, errors.New("could not create new mongocrypt object")
 	}
+	C.mongocrypt_setopt_retry_kms(wrapped, true)
 	httpClient := opts.HTTPClient
 	if httpClient == nil {
 		httpClient = httputil.DefaultHTTPClient
@@ -85,7 +86,7 @@ func NewMongoCrypt(opts *options.MongoCryptOptions) (*MongoCrypt, error) {
 	}
 
 	if opts.BypassQueryAnalysis {
-		C.mongocrypt_setopt_bypass_query_analysis(wrapped)
+		C.mongocrypt_setopt_bypass_query_analysis(crypt.wrapped)
 	}
 
 	// If loading the crypt_shared library isn't disabled, set the default library search path "$SYSTEM"
diff --git a/x/mongo/driver/mongocrypt/mongocrypt_kms_context.go b/x/mongo/driver/mongocrypt/mongocrypt_kms_context.go
index 296a22315c..49baa37f2e 100644
--- a/x/mongo/driver/mongocrypt/mongocrypt_kms_context.go
+++ b/x/mongo/driver/mongocrypt/mongocrypt_kms_context.go
@@ -11,6 +11,7 @@ package mongocrypt
 
 // #include <mongocrypt.h>
 import "C"
+import "time"
 
 // KmsContext represents a mongocrypt_kms_ctx_t handle.
 type KmsContext struct {
@@ -41,6 +42,8 @@ func (kc *KmsContext) KMSProvider() string {
 
 // Message returns the message to send to the KMS.
 func (kc *KmsContext) Message() ([]byte, error) {
+	time.Sleep(time.Duration(C.mongocrypt_kms_ctx_usleep(kc.wrapped)) * time.Microsecond)
+
 	msgBinary := newBinary()
 	defer msgBinary.close()
 
@@ -74,3 +77,11 @@ func (kc *KmsContext) createErrorFromStatus() error {
 	C.mongocrypt_kms_ctx_status(kc.wrapped, status)
 	return errorFromStatus(status)
 }
+
+// RequestError returns the source of the network error for KMS requests.
+func (kc *KmsContext) RequestError() error {
+	if bool(C.mongocrypt_kms_ctx_fail(kc.wrapped)) {
+		return nil
+	}
+	return kc.createErrorFromStatus()
+}
diff --git a/x/mongo/driver/mongocrypt/mongocrypt_kms_context_not_enabled.go b/x/mongo/driver/mongocrypt/mongocrypt_kms_context_not_enabled.go
index 6bce2f0299..7968897648 100644
--- a/x/mongo/driver/mongocrypt/mongocrypt_kms_context_not_enabled.go
+++ b/x/mongo/driver/mongocrypt/mongocrypt_kms_context_not_enabled.go
@@ -37,3 +37,8 @@ func (kc *KmsContext) BytesNeeded() int32 {
 func (kc *KmsContext) FeedResponse([]byte) error {
 	panic(cseNotSupportedMsg)
 }
+
+// RequestError returns the source of the network error for KMS requests.
+func (kc *KmsContext) RequestError() error {
+	panic(cseNotSupportedMsg)
+}