diff --git a/plugin/src/software/aws/toolkits/eclipse/amazonq/exception/LspError.java b/plugin/src/software/aws/toolkits/eclipse/amazonq/exception/LspError.java
index 7e18fad6..7ac039fe 100644
--- a/plugin/src/software/aws/toolkits/eclipse/amazonq/exception/LspError.java
+++ b/plugin/src/software/aws/toolkits/eclipse/amazonq/exception/LspError.java
@@ -13,12 +13,16 @@ public enum LspError {
     INVALID_REMOTE_SERVER("Invalid Remote Server"),
     INVALID_CACHE_SERVER("Invalid Cache Server"),
     MANIFEST_FETCH_ERROR("Error fetching manifest"),
+    MANIFEST_REMOTE_FETCH_ERROR("Error fetching manifest from remote location"),
     SERVER_FETCH_ERROR("Error fetching server"),
     UNEXPECTED_CACHE_ERROR("Error while caching file"),
+    UNEXPECTED_MANIFEST_CACHE_ERROR("Error while caching Manifest file"),
     NO_COMPATIBLE_LSP("No LSP version found matching requirements"),
+    NO_VALID_SERVER_FALLBACK("No valid server version to fallback to."),
+    ARTIFACT_VALIDATION_ERROR("Error validating artifact"),
     INVALID_LAUNCH_PROPERTIES("Invalid launch properties"),
     INVALID_WORKING_DIRECTORY("Invalid working directory"),
-    EXTRACTION_ERROR("Error or invalid zip files"),
+    SERVER_ZIP_EXTRACTION_ERROR("Error extracting server zip files"),
     UNKNOWN("Unknown");
 
     private final String value;
diff --git a/plugin/src/software/aws/toolkits/eclipse/amazonq/lsp/manager/fetcher/RemoteLspFetcher.java b/plugin/src/software/aws/toolkits/eclipse/amazonq/lsp/manager/fetcher/RemoteLspFetcher.java
index b297ee12..37382e96 100644
--- a/plugin/src/software/aws/toolkits/eclipse/amazonq/lsp/manager/fetcher/RemoteLspFetcher.java
+++ b/plugin/src/software/aws/toolkits/eclipse/amazonq/lsp/manager/fetcher/RemoteLspFetcher.java
@@ -141,7 +141,7 @@ public LspFetchResult fetch(final PluginPlatform platform, final PluginArchitect
         }
 
         String failureReason = "Unable to find a compatible version of Amazon Q Language Server.";
-        setErrorReason(LspError.NO_COMPATIBLE_LSP.toString());
+        setErrorReason(LspError.NO_VALID_SERVER_FALLBACK.toString());
         emitGetServer(Result.FAILED, null, LanguageServerLocation.UNKNOWN, start);
         throw new AmazonQPluginException(failureReason);
     }
@@ -260,12 +260,14 @@ private boolean downloadContentFromRemote(final Content content, final Path down
                     return true;
                 } else {
                     ArtifactUtils.deleteDirectory(tempFolder);
+                    setErrorReason(LspError.ARTIFACT_VALIDATION_ERROR.toString());
                 }
             } else {
                 setErrorReason(LspError.SERVER_FETCH_ERROR + "-" + response.statusCode());
                 throw new AmazonQPluginException("Failed to download remote LSP artifact. Response code: " + response.statusCode());
             }
         } catch (Exception ex) {
+            //TODO: account for these failures in telemtry emissions
             Activator.getLogger().error("Error downloading from remote", ex);
         }
         return false;
@@ -283,7 +285,7 @@ private boolean extractZipFilesFromRemote(final Path downloadDirectory) {
         } catch (Exception e) {
             String errorMessage = String.format("Failed to extract zip files in %s", downloadDirectory);
             Activator.getLogger().error(errorMessage, e);
-            setErrorReason(LspError.EXTRACTION_ERROR.toString());
+            setErrorReason(LspError.SERVER_ZIP_EXTRACTION_ERROR.toString());
             return false;
         }
     }
@@ -298,7 +300,7 @@ private boolean extractZip(final Path zipFile, final Path downloadDirectory) {
             ArtifactUtils.extractFile(zipFile, unzipFolder);
         } catch (IOException e) {
             Activator.getLogger().error(String.format("Failed to extract zip contents for: %s, some features may not work", zipFile.toString()), e);
-            setErrorReason(ExceptionMetadata.scrubException(LspError.EXTRACTION_ERROR.toString(), e));
+            setErrorReason(ExceptionMetadata.scrubException(LspError.SERVER_ZIP_EXTRACTION_ERROR.toString(), e));
             return false;
         }
         return true;
diff --git a/plugin/src/software/aws/toolkits/eclipse/amazonq/lsp/manager/fetcher/VersionManifestFetcher.java b/plugin/src/software/aws/toolkits/eclipse/amazonq/lsp/manager/fetcher/VersionManifestFetcher.java
index 2a8cdf3b..b586323c 100644
--- a/plugin/src/software/aws/toolkits/eclipse/amazonq/lsp/manager/fetcher/VersionManifestFetcher.java
+++ b/plugin/src/software/aws/toolkits/eclipse/amazonq/lsp/manager/fetcher/VersionManifestFetcher.java
@@ -117,7 +117,7 @@ private Optional<Manifest> getResourceFromCache() {
             }
         } catch (Exception e) {
             Activator.getLogger().error("Error fetching resource from cache", e);
-            emitGetManifest(null, ManifestLocation.CACHE, ExceptionMetadata.scrubException(LspError.MANIFEST_FETCH_ERROR.toString(), e));
+            emitGetManifest(null, ManifestLocation.CACHE, ExceptionMetadata.scrubException(LspError.UNEXPECTED_MANIFEST_CACHE_ERROR.toString(), e));
         }
         return Optional.empty();
     }
@@ -176,7 +176,7 @@ private Optional<Manifest> validateAndCacheLatest(final HttpResponse<String> res
             return manifest;
         } catch (Exception e) {
             Activator.getLogger().error("Failed to cache manifest file", e);
-            emitGetManifest(null, ManifestLocation.REMOTE, ExceptionMetadata.scrubException(LspError.UNEXPECTED_CACHE_ERROR.toString(), e));
+            emitGetManifest(null, ManifestLocation.REMOTE, ExceptionMetadata.scrubException(LspError.MANIFEST_REMOTE_FETCH_ERROR.toString(), e));
         }
         return Optional.empty();
     }