diff --git a/src/main/java/io/cryostat/net/web/WebServer.java b/src/main/java/io/cryostat/net/web/WebServer.java
index 3773efbcdf..b5bc435d6c 100644
--- a/src/main/java/io/cryostat/net/web/WebServer.java
+++ b/src/main/java/io/cryostat/net/web/WebServer.java
@@ -90,6 +90,7 @@ public class WebServer extends AbstractVerticle {
 
     // Use X- prefix so as to not trigger web-browser auth dialogs
     public static final String AUTH_SCHEME_HEADER = "X-WWW-Authenticate";
+    public static final String DATASOURCE_FILENAME = "cryostat-analysis.jfr";
 
     private final HttpServer server;
     private final NetworkConfiguration netConf;
diff --git a/src/main/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostFromPathHandler.java b/src/main/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostFromPathHandler.java
index 6d33709476..55488afbee 100644
--- a/src/main/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostFromPathHandler.java
+++ b/src/main/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostFromPathHandler.java
@@ -55,6 +55,7 @@
 import io.cryostat.core.sys.Environment;
 import io.cryostat.net.AuthManager;
 import io.cryostat.net.security.ResourceAction;
+import io.cryostat.net.web.WebServer;
 import io.cryostat.net.web.http.HttpMimeType;
 import io.cryostat.net.web.http.HttpModule;
 import io.cryostat.net.web.http.api.ApiVersion;
@@ -188,13 +189,14 @@ private ResponseMessage doPost(String subdirectoryName, String recordingName, UR
                 MultipartForm.create()
                         .binaryFileUpload(
                                 "file",
-                                recordingName,
+                                WebServer.DATASOURCE_FILENAME,
                                 recordingPath.toString(),
                                 HttpMimeType.OCTET_STREAM.toString());
 
         CompletableFuture<ResponseMessage> future = new CompletableFuture<>();
         webClient
                 .postAbs(uploadUrl.toURI().resolve("/load").normalize().toString())
+                .addQueryParam("overwrite", "true")
                 .timeout(TimeUnit.SECONDS.toMillis(httpTimeoutSeconds))
                 .sendMultipartForm(
                         form,
diff --git a/src/main/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostHandler.java b/src/main/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostHandler.java
index dcbae79f33..cd6204a07a 100644
--- a/src/main/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostHandler.java
+++ b/src/main/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostHandler.java
@@ -55,6 +55,7 @@
 import io.cryostat.core.sys.Environment;
 import io.cryostat.net.AuthManager;
 import io.cryostat.net.security.ResourceAction;
+import io.cryostat.net.web.WebServer;
 import io.cryostat.net.web.http.HttpMimeType;
 import io.cryostat.net.web.http.HttpModule;
 import io.cryostat.net.web.http.api.ApiVersion;
@@ -188,13 +189,14 @@ private ResponseMessage doPost(String sourceTarget, String recordingName, URL up
                 MultipartForm.create()
                         .binaryFileUpload(
                                 "file",
-                                recordingName,
+                                WebServer.DATASOURCE_FILENAME,
                                 recordingPath.toString(),
                                 HttpMimeType.OCTET_STREAM.toString());
 
         CompletableFuture<ResponseMessage> future = new CompletableFuture<>();
         webClient
                 .postAbs(uploadUrl.toURI().resolve("/load").normalize().toString())
+                .addQueryParam("overwrite", "true")
                 .timeout(TimeUnit.SECONDS.toMillis(httpTimeoutSeconds))
                 .sendMultipartForm(
                         form,
diff --git a/src/main/java/io/cryostat/net/web/http/api/v1/RecordingUploadPostHandler.java b/src/main/java/io/cryostat/net/web/http/api/v1/RecordingUploadPostHandler.java
index eb54503ac5..3e92b363c5 100644
--- a/src/main/java/io/cryostat/net/web/http/api/v1/RecordingUploadPostHandler.java
+++ b/src/main/java/io/cryostat/net/web/http/api/v1/RecordingUploadPostHandler.java
@@ -57,6 +57,7 @@
 import io.cryostat.net.AuthManager;
 import io.cryostat.net.security.ResourceAction;
 import io.cryostat.net.web.DeprecatedApi;
+import io.cryostat.net.web.WebServer;
 import io.cryostat.net.web.http.AbstractAuthenticatedRequestHandler;
 import io.cryostat.net.web.http.HttpMimeType;
 import io.cryostat.net.web.http.HttpModule;
@@ -179,13 +180,14 @@ private ResponseMessage doPost(String recordingName, URL uploadUrl) throws Excep
                 MultipartForm.create()
                         .binaryFileUpload(
                                 "file",
-                                recordingName,
+                                WebServer.DATASOURCE_FILENAME,
                                 recordingPath.toString(),
                                 HttpMimeType.OCTET_STREAM.toString());
 
         CompletableFuture<ResponseMessage> future = new CompletableFuture<>();
         webClient
                 .postAbs(uploadUrl.toURI().resolve("/load").normalize().toString())
+                .addQueryParam("overwrite", "true")
                 .timeout(TimeUnit.SECONDS.toMillis(httpTimeoutSeconds))
                 .sendMultipartForm(
                         form,
diff --git a/src/main/java/io/cryostat/net/web/http/api/v1/TargetRecordingUploadPostHandler.java b/src/main/java/io/cryostat/net/web/http/api/v1/TargetRecordingUploadPostHandler.java
index f781af5c10..43f7172885 100644
--- a/src/main/java/io/cryostat/net/web/http/api/v1/TargetRecordingUploadPostHandler.java
+++ b/src/main/java/io/cryostat/net/web/http/api/v1/TargetRecordingUploadPostHandler.java
@@ -61,6 +61,7 @@
 import io.cryostat.net.AuthManager;
 import io.cryostat.net.TargetConnectionManager;
 import io.cryostat.net.security.ResourceAction;
+import io.cryostat.net.web.WebServer;
 import io.cryostat.net.web.http.AbstractAuthenticatedRequestHandler;
 import io.cryostat.net.web.http.HttpMimeType;
 import io.cryostat.net.web.http.HttpModule;
@@ -185,7 +186,7 @@ private ResponseMessage doPost(RoutingContext ctx, URL uploadUrl) throws Excepti
                 MultipartForm.create()
                         .binaryFileUpload(
                                 "file",
-                                recordingName,
+                                WebServer.DATASOURCE_FILENAME,
                                 recordingPath.toString(),
                                 HttpMimeType.OCTET_STREAM.toString());
 
@@ -193,6 +194,7 @@ private ResponseMessage doPost(RoutingContext ctx, URL uploadUrl) throws Excepti
         try {
             webClient
                     .postAbs(uploadUrl.toURI().resolve("/load").normalize().toString())
+                    .addQueryParam("overwrite", "true")
                     .timeout(TimeUnit.SECONDS.toMillis(httpTimeoutSeconds))
                     .sendMultipartForm(
                             form,
diff --git a/src/test/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostFromPathHandlerTest.java b/src/test/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostFromPathHandlerTest.java
index 0d9fc74492..89f8d0cc2c 100644
--- a/src/test/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostFromPathHandlerTest.java
+++ b/src/test/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostFromPathHandlerTest.java
@@ -222,6 +222,8 @@ void shouldDoUpload() throws Exception {
             HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
             HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
             when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+            when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                    .thenReturn(httpReq);
             when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
             Mockito.doAnswer(
                             new Answer<Void>() {
@@ -275,6 +277,8 @@ void shouldHandleInvalidResponseStatusCode() throws Exception {
             HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
             when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
             when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
+            when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                    .thenReturn(httpReq);
             Mockito.doAnswer(
                             new Answer<Void>() {
                                 @Override
@@ -333,6 +337,8 @@ void shouldHandleNullStatusMessage() throws Exception {
             HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
             HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
             when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+            when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                    .thenReturn(httpReq);
             when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
             Mockito.doAnswer(
                             new Answer<Void>() {
@@ -392,6 +398,8 @@ void shouldHandleNullResponseBody() throws Exception {
             HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
             HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
             when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+            when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                    .thenReturn(httpReq);
             when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
             Mockito.doAnswer(
                             new Answer<Void>() {
diff --git a/src/test/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostHandlerTest.java b/src/test/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostHandlerTest.java
index fb2a320940..dd7277fa75 100644
--- a/src/test/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostHandlerTest.java
+++ b/src/test/java/io/cryostat/net/web/http/api/beta/RecordingUploadPostHandlerTest.java
@@ -215,6 +215,8 @@ void shouldDoUpload() throws Exception {
             HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
             HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
             when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+            when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                    .thenReturn(httpReq);
             when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
             Mockito.doAnswer(
                             new Answer<Void>() {
@@ -264,6 +266,8 @@ void shouldHandleInvalidResponseStatusCode() throws Exception {
             HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
             HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
             when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+            when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                    .thenReturn(httpReq);
             when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
             Mockito.doAnswer(
                             new Answer<Void>() {
@@ -320,6 +324,8 @@ void shouldHandleNullStatusMessage() throws Exception {
             HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
             HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
             when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+            when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                    .thenReturn(httpReq);
             when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
             Mockito.doAnswer(
                             new Answer<Void>() {
@@ -376,6 +382,8 @@ void shouldHandleNullResponseBody() throws Exception {
             HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
             HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
             when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+            when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                    .thenReturn(httpReq);
             when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
             Mockito.doAnswer(
                             new Answer<Void>() {
diff --git a/src/test/java/io/cryostat/net/web/http/api/v1/RecordingUploadPostHandlerTest.java b/src/test/java/io/cryostat/net/web/http/api/v1/RecordingUploadPostHandlerTest.java
index 77fad75d59..71f1f4e2a3 100644
--- a/src/test/java/io/cryostat/net/web/http/api/v1/RecordingUploadPostHandlerTest.java
+++ b/src/test/java/io/cryostat/net/web/http/api/v1/RecordingUploadPostHandlerTest.java
@@ -195,6 +195,8 @@ void shouldDoUpload() throws Exception {
         HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
         HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
         Mockito.when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+        Mockito.when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                .thenReturn(httpReq);
         Mockito.when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
         Mockito.doAnswer(
                         new Answer<Void>() {
@@ -251,6 +253,8 @@ void shouldHandleInvalidResponseStatusCode() throws Exception {
         HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
         HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
         Mockito.when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+        Mockito.when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                .thenReturn(httpReq);
         Mockito.when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
         Mockito.doAnswer(
                         new Answer<Void>() {
@@ -316,6 +320,8 @@ void shouldHandleNullStatusMessage() throws Exception {
         HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
         HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
         Mockito.when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+        Mockito.when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                .thenReturn(httpReq);
         Mockito.when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
         Mockito.doAnswer(
                         new Answer<Void>() {
@@ -374,6 +380,8 @@ void shouldHandleNullResponseBody() throws Exception {
         HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
         HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
         Mockito.when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+        Mockito.when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                .thenReturn(httpReq);
         Mockito.when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
         Mockito.doAnswer(
                         new Answer<Void>() {
diff --git a/src/test/java/io/cryostat/net/web/http/api/v1/TargetRecordingUploadPostHandlerTest.java b/src/test/java/io/cryostat/net/web/http/api/v1/TargetRecordingUploadPostHandlerTest.java
index fefd14530d..6b03ca36b8 100644
--- a/src/test/java/io/cryostat/net/web/http/api/v1/TargetRecordingUploadPostHandlerTest.java
+++ b/src/test/java/io/cryostat/net/web/http/api/v1/TargetRecordingUploadPostHandlerTest.java
@@ -232,6 +232,8 @@ void shouldDoUpload() throws Exception {
         HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
         HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
         Mockito.when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+        Mockito.when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                .thenReturn(httpReq);
         Mockito.when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
         Mockito.doAnswer(
                         new Answer<Void>() {
@@ -301,6 +303,8 @@ void shouldHandleInvalidResponseStatusCode() throws Exception {
         HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
         HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
         Mockito.when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+        Mockito.when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                .thenReturn(httpReq);
         Mockito.when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
         Mockito.doAnswer(
                         new Answer<Void>() {
@@ -373,6 +377,8 @@ void shouldHandleNullStatusMessage() throws Exception {
         HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
         HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
         Mockito.when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+        Mockito.when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                .thenReturn(httpReq);
         Mockito.when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
         Mockito.doAnswer(
                         new Answer<Void>() {
@@ -445,6 +451,8 @@ void shouldHandleNullResponseBody() throws Exception {
         HttpRequest<Buffer> httpReq = Mockito.mock(HttpRequest.class);
         HttpResponse<Buffer> httpResp = Mockito.mock(HttpResponse.class);
         Mockito.when(webClient.postAbs(Mockito.anyString())).thenReturn(httpReq);
+        Mockito.when(httpReq.addQueryParam(Mockito.anyString(), Mockito.anyString()))
+                .thenReturn(httpReq);
         Mockito.when(httpReq.timeout(Mockito.anyLong())).thenReturn(httpReq);
         Mockito.doAnswer(
                         new Answer<Void>() {
diff --git a/src/test/java/itest/UploadRecordingIT.java b/src/test/java/itest/UploadRecordingIT.java
index bac98cbf40..9efa408ca0 100644
--- a/src/test/java/itest/UploadRecordingIT.java
+++ b/src/test/java/itest/UploadRecordingIT.java
@@ -45,6 +45,7 @@
 import java.util.concurrent.TimeUnit;
 import java.util.concurrent.TimeoutException;
 
+import io.cryostat.net.web.WebServer;
 import io.cryostat.net.web.http.HttpMimeType;
 
 import io.vertx.core.MultiMap;
@@ -131,7 +132,9 @@ public void shouldLoadRecordingToDatasource() throws Exception {
                         });
 
         final String expectedUploadResponse =
-                String.format("Uploaded: %s\nSet: %s", RECORDING_NAME, RECORDING_NAME);
+                String.format(
+                        "Uploaded: %s\nSet: %s",
+                        WebServer.DATASOURCE_FILENAME, WebServer.DATASOURCE_FILENAME);
 
         MatcherAssert.assertThat(
                 uploadRespFuture.get().trim(), Matchers.equalTo(expectedUploadResponse));
@@ -154,7 +157,7 @@ public void shouldLoadRecordingToDatasource() throws Exception {
 
         MatcherAssert.assertThat(
                 getRespFuture.get().trim(),
-                Matchers.equalTo(String.format("**%s**", RECORDING_NAME)));
+                Matchers.equalTo(String.format("**%s**", WebServer.DATASOURCE_FILENAME)));
 
         // Query Data Source for recording metrics
         final CompletableFuture<JsonArray> queryRespFuture = new CompletableFuture<>();