diff --git a/client/cmd/install.go b/client/cmd/install.go
index 4fe55f59..b4d12049 100644
--- a/client/cmd/install.go
+++ b/client/cmd/install.go
@@ -21,7 +21,6 @@ import (
 	"github.com/ddworken/hishtory/shared"
 	"github.com/google/uuid"
 	"github.com/spf13/cobra"
-	"gorm.io/gorm"
 )
 
 var offlineInit *bool
@@ -41,7 +40,7 @@ var installCmd = &cobra.Command{
 		if os.Getenv("HISHTORY_SKIP_INIT_IMPORT") == "" {
 			db, err := hctx.OpenLocalSqliteDb()
 			lib.CheckFatalError(err)
-			count, err := countStoredEntries(db)
+			count, err := lib.CountStoredEntries(db)
 			lib.CheckFatalError(err)
 			if count < 10 {
 				fmt.Println("Importing existing shell history...")
@@ -65,7 +64,7 @@ var initCmd = &cobra.Command{
 	Run: func(cmd *cobra.Command, args []string) {
 		db, err := hctx.OpenLocalSqliteDb()
 		lib.CheckFatalError(err)
-		count, err := countStoredEntries(db)
+		count, err := lib.CountStoredEntries(db)
 		lib.CheckFatalError(err)
 		if count > 0 {
 			fmt.Printf("Your current hishtory profile has saved history entries, are you sure you want to run `init` and reset?\nNote: This won't clear any imported history entries from your existing shell\n[y/N]")
@@ -128,13 +127,6 @@ var uninstallCmd = &cobra.Command{
 	},
 }
 
-func countStoredEntries(db *gorm.DB) (int64, error) {
-	return lib.RetryingDbFunctionWithResult(func() (int64, error) {
-		var count int64
-		return count, db.Model(&data.HistoryEntry{}).Count(&count).Error
-	})
-}
-
 func warnIfUnsupportedBashVersion() error {
 	_, err := exec.LookPath("bash")
 	if err != nil {
diff --git a/client/lib/lib.go b/client/lib/lib.go
index 6c85e3f3..4d3851bd 100644
--- a/client/lib/lib.go
+++ b/client/lib/lib.go
@@ -669,32 +669,59 @@ func Reupload(ctx context.Context) error {
 	if config.IsOffline {
 		return nil
 	}
-	entries, err := Search(ctx, hctx.GetDb(ctx), "", 0)
+	numEntries, err := CountStoredEntries(hctx.GetDb(ctx))
 	if err != nil {
-		return fmt.Errorf("failed to reupload due to failed search: %w", err)
+		return fmt.Errorf("failed to upload history entries due to error in counting entries: %v", err)
 	}
 	var bar *progressbar.ProgressBar
-	if len(entries) > NUM_IMPORTED_ENTRIES_SLOW {
+	if numEntries > int64(NUM_IMPORTED_ENTRIES_SLOW) {
 		fmt.Println("Persisting history entries")
-		bar = progressbar.Default(int64(len(entries)))
+		bar = progressbar.Default(int64(numEntries))
 		defer bar.Finish()
 	}
-	chunkSize := 500
-	chunks := shared.Chunks(entries, chunkSize)
-	return shared.ForEach(chunks, 10, func(chunk []*data.HistoryEntry) error {
-		jsonValue, err := EncryptAndMarshal(config, chunk)
+
+	// This number is a balance between speed and memory usage. If we make it too high, then
+	// it will mean we use a ton of memory (since we retrieve all of those entries). But if
+	// we make it too low, then it will have to do repeated SQL queries with OFFSETs, which
+	// are inherently slow.
+	searchChunkSize := 300_000
+	currentOffset := 0
+	for {
+		entries, err := SearchWithOffset(ctx, hctx.GetDb(ctx), "", searchChunkSize, currentOffset)
 		if err != nil {
-			return fmt.Errorf("failed to reupload due to failed encryption: %w", err)
+			return fmt.Errorf("failed to reupload due to failed search: %w", err)
 		}
-		_, err = ApiPost(ctx, "/api/v1/submit?source_device_id="+config.DeviceId, "application/json", jsonValue)
-		if err != nil {
-			return fmt.Errorf("failed to reupload due to failed POST: %w", err)
+		if len(entries) == 0 {
+			if currentOffset == 0 && numEntries != 0 {
+				return fmt.Errorf("found no entries for reuploading, something went wrong")
+			} else {
+				return nil
+			}
 		}
-		if bar != nil {
-			_ = bar.Add(chunkSize)
+		currentOffset += searchChunkSize
+		// This number is a balance between speed, and ensuring that we don't send too much data
+		// in a single request (since large individual requests are extremely slow). From benchmarking,
+		// it is apparent that this value seems to work quite well.
+		uploadChunkSize := 500
+		chunks := shared.Chunks(entries, uploadChunkSize)
+		err = shared.ForEach(chunks, 10, func(chunk []*data.HistoryEntry) error {
+			jsonValue, err := EncryptAndMarshal(config, chunk)
+			if err != nil {
+				return fmt.Errorf("failed to reupload due to failed encryption: %w", err)
+			}
+			_, err = ApiPost(ctx, "/api/v1/submit?source_device_id="+config.DeviceId, "application/json", jsonValue)
+			if err != nil {
+				return fmt.Errorf("failed to reupload due to failed POST: %w", err)
+			}
+			if bar != nil {
+				_ = bar.Add(uploadChunkSize)
+			}
+			return nil
+		})
+		if err != nil {
+			return err
 		}
-		return nil
-	})
+	}
 }
 
 func RetrieveAdditionalEntriesFromRemote(ctx context.Context, queryReason string) error {
@@ -832,12 +859,16 @@ func MakeWhereQueryFromSearch(ctx context.Context, db *gorm.DB, query string) (*
 }
 
 func Search(ctx context.Context, db *gorm.DB, query string, limit int) ([]*data.HistoryEntry, error) {
-	return retryingSearch(ctx, db, query, limit, 0)
+	return SearchWithOffset(ctx, db, query, limit, 0)
+}
+
+func SearchWithOffset(ctx context.Context, db *gorm.DB, query string, limit, offset int) ([]*data.HistoryEntry, error) {
+	return retryingSearch(ctx, db, query, limit, offset, 0)
 }
 
 const SEARCH_RETRY_COUNT = 3
 
-func retryingSearch(ctx context.Context, db *gorm.DB, query string, limit int, currentRetryNum int) ([]*data.HistoryEntry, error) {
+func retryingSearch(ctx context.Context, db *gorm.DB, query string, limit, offset int, currentRetryNum int) ([]*data.HistoryEntry, error) {
 	if ctx == nil && query != "" {
 		return nil, fmt.Errorf("lib.Search called with a nil context and a non-empty query (this should never happen)")
 	}
@@ -855,13 +886,16 @@ func retryingSearch(ctx context.Context, db *gorm.DB, query string, limit int, c
 	if limit > 0 {
 		tx = tx.Limit(limit)
 	}
+	if offset > 0 {
+		tx = tx.Offset(offset)
+	}
 	var historyEntries []*data.HistoryEntry
 	result := tx.Find(&historyEntries)
 	if result.Error != nil {
 		if strings.Contains(result.Error.Error(), SQLITE_LOCKED_ERR_MSG) && currentRetryNum < SEARCH_RETRY_COUNT {
 			hctx.GetLogger().Infof("Ignoring err=%v and retrying search query, cnt=%d", result.Error, currentRetryNum)
 			time.Sleep(time.Duration(currentRetryNum*rand.Intn(50)) * time.Millisecond)
-			return retryingSearch(ctx, db, query, limit, currentRetryNum+1)
+			return retryingSearch(ctx, db, query, limit, offset, currentRetryNum+1)
 		}
 		return nil, fmt.Errorf("DB query error: %w", result.Error)
 	}
@@ -1069,3 +1103,10 @@ func SendDeletionRequest(ctx context.Context, deletionRequest shared.DeletionReq
 	}
 	return nil
 }
+
+func CountStoredEntries(db *gorm.DB) (int64, error) {
+	return RetryingDbFunctionWithResult(func() (int64, error) {
+		var count int64
+		return count, db.Model(&data.HistoryEntry{}).Count(&count).Error
+	})
+}
diff --git a/shared/testutils/testutils.go b/shared/testutils/testutils.go
index 163ce697..b0a9e4ca 100644
--- a/shared/testutils/testutils.go
+++ b/shared/testutils/testutils.go
@@ -86,6 +86,7 @@ func BackupAndRestoreWithId(t testing.TB, id string) func() {
 		path.Join(homedir, data.GetHishtoryPath(), "hishtory"),
 		path.Join(homedir, ".bash_history"),
 		path.Join(homedir, ".zsh_history"),
+		path.Join(homedir, ".zhistory"),
 		path.Join(homedir, ".local/share/fish/fish_history"),
 	}
 	for _, file := range renameFiles {