diff --git a/lldb/source/API/SBProcess.cpp b/lldb/source/API/SBProcess.cpp
index 020e5be0ec575..05ae9b50a29b0 100644
--- a/lldb/source/API/SBProcess.cpp
+++ b/lldb/source/API/SBProcess.cpp
@@ -1039,8 +1039,11 @@ SBStructuredData SBProcess::GetExtendedCrashInformation() {
   auto expected_data =
       platform_sp->FetchExtendedCrashInformation(*process_sp.get());
 
-  if (!expected_data)
+  if (!expected_data) {
+    LLDB_LOG_ERROR(GetLog(LLDBLog::API), expected_data.takeError(),
+                   "FetchExtendedCrashInformation failed: {0}");
     return data;
+  }
 
   StructuredData::ObjectSP fetched_data = *expected_data;
   data.m_impl_up->SetObjectSP(fetched_data);
diff --git a/lldb/source/Host/posix/MainLoopPosix.cpp b/lldb/source/Host/posix/MainLoopPosix.cpp
index c6fe7814bd22e..b84411d3aa754 100644
--- a/lldb/source/Host/posix/MainLoopPosix.cpp
+++ b/lldb/source/Host/posix/MainLoopPosix.cpp
@@ -9,6 +9,7 @@
 #include "lldb/Host/posix/MainLoopPosix.h"
 #include "lldb/Host/Config.h"
 #include "lldb/Host/PosixApi.h"
+#include "lldb/Utility/LLDBLog.h"
 #include "lldb/Utility/Status.h"
 #include "llvm/Config/llvm-config.h"
 #include "llvm/Support/Errno.h"
@@ -392,6 +393,11 @@ bool MainLoopPosix::Interrupt() {
     return true;
 
   char c = '.';
-  llvm::Expected<size_t> result = m_interrupt_pipe.Write(&c, 1);
-  return result && *result != 0;
+  llvm::Expected<size_t> result_or_err = m_interrupt_pipe.Write(&c, 1);
+  if (!result_or_err) {
+    LLDB_LOG_ERROR(GetLog(LLDBLog::Host), result_or_err.takeError(),
+                   "interrupt pipe write failed: {0}");
+    return false;
+  }
+  return *result_or_err != 0;
 }
diff --git a/lldb/source/Interpreter/ScriptInterpreter.cpp b/lldb/source/Interpreter/ScriptInterpreter.cpp
index 5165e93abe315..77818f1a32ca4 100644
--- a/lldb/source/Interpreter/ScriptInterpreter.cpp
+++ b/lldb/source/Interpreter/ScriptInterpreter.cpp
@@ -263,7 +263,7 @@ ScriptInterpreterIORedirect::Create(bool enable_io, Debugger &debugger,
   auto nullout = FileSystem::Instance().Open(FileSpec(FileSystem::DEV_NULL),
                                              File::eOpenOptionWriteOnly);
   if (!nullout)
-    return nullin.takeError();
+    return nullout.takeError();
 
   return std::unique_ptr<ScriptInterpreterIORedirect>(
       new ScriptInterpreterIORedirect(std::move(*nullin), std::move(*nullout)));
diff --git a/lldb/source/Plugins/Language/CPlusPlus/LibStdcpp.cpp b/lldb/source/Plugins/Language/CPlusPlus/LibStdcpp.cpp
index 4055dc2fd9503..633f7ebf8199a 100644
--- a/lldb/source/Plugins/Language/CPlusPlus/LibStdcpp.cpp
+++ b/lldb/source/Plugins/Language/CPlusPlus/LibStdcpp.cpp
@@ -17,6 +17,7 @@
 #include "lldb/Target/Target.h"
 #include "lldb/Utility/DataBufferHeap.h"
 #include "lldb/Utility/Endian.h"
+#include "lldb/Utility/LLDBLog.h"
 #include "lldb/Utility/Status.h"
 #include "lldb/Utility/Stream.h"
 #include "lldb/ValueObject/ValueObject.h"
diff --git a/lldb/source/Plugins/Process/minidump/ProcessMinidump.cpp b/lldb/source/Plugins/Process/minidump/ProcessMinidump.cpp
index f836710033b09..7c0253450e071 100644
--- a/lldb/source/Plugins/Process/minidump/ProcessMinidump.cpp
+++ b/lldb/source/Plugins/Process/minidump/ProcessMinidump.cpp
@@ -213,17 +213,23 @@ Status ProcessMinidump::DoLoadCore() {
 
   m_thread_list = m_minidump_parser->GetThreads();
   auto exception_stream_it = m_minidump_parser->GetExceptionStreams();
-  for (auto exception_stream : exception_stream_it) {
+  for (auto exception_stream_or_err : exception_stream_it) {
     // If we can't read an exception stream skip it
     // We should probably serve a warning
-    if (!exception_stream)
+    if (!exception_stream_or_err) {
+      LLDB_LOG_ERROR(GetLog(LLDBLog::Process),
+                     exception_stream_or_err.takeError(),
+                     "failed to read exception stream: {0}");
       continue;
+    }
+    const llvm::minidump::ExceptionStream &exception_stream =
+        *exception_stream_or_err;
 
     if (!m_exceptions_by_tid
-             .try_emplace(exception_stream->ThreadId, exception_stream.get())
+             .try_emplace(exception_stream.ThreadId, exception_stream)
              .second) {
       return Status::FromErrorStringWithFormatv(
-          "Duplicate exception stream for tid {0}", exception_stream->ThreadId);
+          "Duplicate exception stream for tid {0}", exception_stream.ThreadId);
     }
   }
 
diff --git a/lldb/source/Plugins/Process/scripted/ScriptedThread.cpp b/lldb/source/Plugins/Process/scripted/ScriptedThread.cpp
index f1d39a85cb18e..d07cb0003ec27 100644
--- a/lldb/source/Plugins/Process/scripted/ScriptedThread.cpp
+++ b/lldb/source/Plugins/Process/scripted/ScriptedThread.cpp
@@ -174,8 +174,7 @@ bool ScriptedThread::LoadArtificialStackFrames() {
         LLVM_PRETTY_FUNCTION,
         llvm::Twine(
             "StackFrame array size (" + llvm::Twine(arr_size) +
-            llvm::Twine(
-                ") is greater than maximum authorized for a StackFrameList."))
+            ") is greater than maximum authorized for a StackFrameList.")
             .str(),
         error, LLDBLog::Thread);
 
@@ -265,8 +264,10 @@ bool ScriptedThread::LoadArtificialStackFrames() {
       if (!frame_from_script_obj_or_err) {
         return ScriptedInterface::ErrorWithMessage<bool>(
             LLVM_PRETTY_FUNCTION,
-            llvm::Twine("Couldn't add artificial frame (" + llvm::Twine(idx) +
-                        llvm::Twine(") to ScriptedThread StackFrameList."))
+            llvm::Twine(
+                "Couldn't add artificial frame (" + llvm::Twine(idx) +
+                llvm::Twine(") to ScriptedThread StackFrameList: ") +
+                llvm::toString(frame_from_script_obj_or_err.takeError()))
                 .str(),
             error, LLDBLog::Thread);
       } else {
diff --git a/lldb/source/Plugins/SymbolFile/NativePDB/PdbAstBuilderClang.cpp b/lldb/source/Plugins/SymbolFile/NativePDB/PdbAstBuilderClang.cpp
index 1b6bbbc2e7ab9..1784481fec54c 100644
--- a/lldb/source/Plugins/SymbolFile/NativePDB/PdbAstBuilderClang.cpp
+++ b/lldb/source/Plugins/SymbolFile/NativePDB/PdbAstBuilderClang.cpp
@@ -24,6 +24,7 @@
 #include "lldb/Core/Module.h"
 #include "lldb/Symbol/ObjectFile.h"
 #include "lldb/Utility/LLDBAssert.h"
+#include "lldb/Utility/LLDBLog.h"
 #include <optional>
 #include <string_view>
 
@@ -909,6 +910,9 @@ clang::FunctionDecl *PdbAstBuilderClang::CreateFunctionDecl(
           index.tpi().findFullDeclForForwardRef(class_index);
       if (eti) {
         tag_record = CVTagRecord::create(index.tpi().getType(*eti)).asTag();
+      } else {
+        LLDB_LOG_ERROR(GetLog(LLDBLog::Symbols), eti.takeError(),
+                       "failed to find full decl for forward ref: {0}");
       }
     }
     if (!tag_record.FieldList.isSimple()) {
diff --git a/lldb/source/Plugins/SymbolFile/NativePDB/SymbolFileNativePDB.cpp b/lldb/source/Plugins/SymbolFile/NativePDB/SymbolFileNativePDB.cpp
index 3b516bd40e8e4..ddb7c3aeda31a 100644
--- a/lldb/source/Plugins/SymbolFile/NativePDB/SymbolFileNativePDB.cpp
+++ b/lldb/source/Plugins/SymbolFile/NativePDB/SymbolFileNativePDB.cpp
@@ -1338,8 +1338,11 @@ bool SymbolFileNativePDB::ParseLineTable(CompileUnit &comp_unit) {
     for (const LineColumnEntry &group : lines) {
       llvm::Expected<uint32_t> file_index_or_err =
           GetFileIndex(*cii, group.NameIndex);
-      if (!file_index_or_err)
+      if (!file_index_or_err) {
+        LLDB_LOG_ERROR(GetLog(LLDBLog::Symbols), file_index_or_err.takeError(),
+                       "failed to get file index for line entry: {0}");
         continue;
+      }
       uint32_t file_index = file_index_or_err.get();
       lldbassert(!group.LineNumbers.empty());
       CompilandIndexItem::GlobalLineTable::Entry line_entry(
@@ -1542,8 +1545,11 @@ void SymbolFileNativePDB::ParseInlineSite(PdbCompilandSymId id,
   FileSpec decl_file;
   llvm::Expected<uint32_t> file_index_or_err =
       GetFileIndex(*cii, inlinee_line.Header->FileID);
-  if (!file_index_or_err)
+  if (!file_index_or_err) {
+    LLDB_LOG_ERROR(GetLog(LLDBLog::Symbols), file_index_or_err.takeError(),
+                   "failed to get file index for inline site: {0}");
     return;
+  }
   uint32_t file_offset = file_index_or_err.get();
   decl_file = files.GetFileSpecAtIndex(file_offset);
   uint32_t decl_line = inlinee_line.Header->SourceLineNum;
@@ -1771,8 +1777,11 @@ size_t SymbolFileNativePDB::ParseSymbolArrayInScope(
 
 void SymbolFileNativePDB::DumpClangAST(Stream &s, llvm::StringRef filter) {
   auto ts_or_err = GetTypeSystemForLanguage(eLanguageTypeC_plus_plus);
-  if (!ts_or_err)
+  if (!ts_or_err) {
+    LLDB_LOG_ERROR(GetLog(LLDBLog::Symbols), ts_or_err.takeError(),
+                   "failed to get C++ type system: {0}");
     return;
+  }
   auto ts = *ts_or_err;
   TypeSystemClang *clang = llvm::dyn_cast_or_null<TypeSystemClang>(ts.get());
   if (!clang)
diff --git a/lldb/source/Plugins/SymbolLocator/Debuginfod/SymbolLocatorDebuginfod.cpp b/lldb/source/Plugins/SymbolLocator/Debuginfod/SymbolLocatorDebuginfod.cpp
index f9aa6b1a98765..4aa0379d5cc19 100644
--- a/lldb/source/Plugins/SymbolLocator/Debuginfod/SymbolLocatorDebuginfod.cpp
+++ b/lldb/source/Plugins/SymbolLocator/Debuginfod/SymbolLocatorDebuginfod.cpp
@@ -174,8 +174,11 @@ GetFileForModule(const ModuleSpec &module_spec,
   PluginProperties &plugin_props = GetGlobalPluginProperties();
   llvm::Expected<std::string> cache_path_or_err = plugin_props.GetCachePath();
   // A cache location is *required*.
-  if (!cache_path_or_err)
+  if (!cache_path_or_err) {
+    LLDB_LOG_ERROR(GetLog(LLDBLog::Symbols), cache_path_or_err.takeError(),
+                   "debuginfod cache path unavailable: {0}");
     return {};
+  }
   std::string cache_path = *cache_path_or_err;
   llvm::SmallVector<llvm::StringRef> debuginfod_urls =
       llvm::getDefaultDebuginfodUrls();
diff --git a/lldb/source/Symbol/SymbolFileOnDemand.cpp b/lldb/source/Symbol/SymbolFileOnDemand.cpp
index 807c2124e48d9..68e5eeaa04295 100644
--- a/lldb/source/Symbol/SymbolFileOnDemand.cpp
+++ b/lldb/source/Symbol/SymbolFileOnDemand.cpp
@@ -515,10 +515,12 @@ SymbolFileOnDemand::GetParameterStackSize(Symbol &symbol) {
     if (log) {
       llvm::Expected<lldb::addr_t> stack_size =
           m_sym_file_impl->GetParameterStackSize(symbol);
-      if (stack_size) {
+      if (stack_size)
         LLDB_LOG(log, "{0} stack size would return for symbol {1} if hydrated.",
                  *stack_size, symbol.GetName());
-      }
+      else
+        LLDB_LOG_ERROR(log, stack_size.takeError(),
+                       "failed to get parameter stack size: {0}");
     }
     return SymbolFile::GetParameterStackSize(symbol);
   }
diff --git a/lldb/source/Target/Statistics.cpp b/lldb/source/Target/Statistics.cpp
index 909f335687b21..46ded78474d25 100644
--- a/lldb/source/Target/Statistics.cpp
+++ b/lldb/source/Target/Statistics.cpp
@@ -17,6 +17,7 @@
 #include "lldb/Target/Process.h"
 #include "lldb/Target/Target.h"
 #include "lldb/Target/UnixSignals.h"
+#include "lldb/Utility/LLDBLog.h"
 #include "lldb/Utility/StructuredData.h"
 
 using namespace lldb;
@@ -498,6 +499,9 @@ llvm::json::Value DebuggerStats::ReportStatistics(
       if (auto json_transcript = llvm::json::parse(buffer))
         global_stats.try_emplace("transcript",
                                  std::move(json_transcript.get()));
+      else
+        LLDB_LOG_ERROR(GetLog(LLDBLog::Target), json_transcript.takeError(),
+                       "failed to parse transcript JSON: {0}");
     }
   }
 
diff --git a/lldb/source/Target/Target.cpp b/lldb/source/Target/Target.cpp
index 0d63f37945b63..f9d83541e5f0e 100644
--- a/lldb/source/Target/Target.cpp
+++ b/lldb/source/Target/Target.cpp
@@ -4267,8 +4267,11 @@ Target::StopHookScripted::HandleStop(ExecutionContext &exc_ctx,
   auto should_stop_or_err = m_interface_sp->HandleStop(exc_ctx, stream);
   output_sp->PutCString(
       reinterpret_cast<StreamString *>(stream.get())->GetData());
-  if (!should_stop_or_err)
+  if (!should_stop_or_err) {
+    LLDB_LOG_ERROR(GetLog(LLDBLog::Target), should_stop_or_err.takeError(),
+                   "scripted stop hook HandleStop failed: {0}");
     return StopHookResult::KeepStopped;
+  }
 
   return *should_stop_or_err ? StopHookResult::KeepStopped
                              : StopHookResult::RequestContinue;
diff --git a/lldb/source/ValueObject/DILEval.cpp b/lldb/source/ValueObject/DILEval.cpp
index 7009bdb42addd..59df936975e07 100644
--- a/lldb/source/ValueObject/DILEval.cpp
+++ b/lldb/source/ValueObject/DILEval.cpp
@@ -12,6 +12,7 @@
 #include "lldb/Symbol/TypeSystem.h"
 #include "lldb/Symbol/VariableList.h"
 #include "lldb/Target/RegisterContext.h"
+#include "lldb/Utility/LLDBLog.h"
 #include "lldb/ValueObject/DILAST.h"
 #include "lldb/ValueObject/DILParser.h"
 #include "lldb/ValueObject/ValueObject.h"
@@ -94,7 +95,7 @@ Interpreter::UnaryConversion(lldb::ValueObjectSP valobj, uint32_t location) {
       llvm::Expected<uint64_t> uint_bit_size =
           uint_type.GetBitSize(m_exe_ctx_scope.get());
       if (!uint_bit_size)
-        return int_bit_size.takeError();
+        return uint_bit_size.takeError();
       if (bitfield_size < *int_bit_size ||
           (in_type.IsSigned() && bitfield_size == *int_bit_size))
         return valobj->CastToBasicType(int_type);
@@ -1098,6 +1099,8 @@ Interpreter::VerifyArithmeticCast(CompilerType source_type,
     } else {
       std::string errMsg = llvm::formatv("unable to get byte size for type {0}",
                                          target_type.TypeDescription());
+      LLDB_LOG_ERROR(GetLog(LLDBLog::Expressions), temp.takeError(),
+                     "GetByteSize failed: {0}");
       return llvm::make_error<DILDiagnosticError>(
           m_expr, std::move(errMsg), location,
           target_type.TypeDescription().length());
@@ -1108,6 +1111,8 @@ Interpreter::VerifyArithmeticCast(CompilerType source_type,
     } else {
       std::string errMsg = llvm::formatv("unable to get byte size for type {0}",
                                          source_type.TypeDescription());
+      LLDB_LOG_ERROR(GetLog(LLDBLog::Expressions), temp.takeError(),
+                     "GetByteSize failed: {0}");
       return llvm::make_error<DILDiagnosticError>(
           m_expr, std::move(errMsg), location,
           source_type.TypeDescription().length());
diff --git a/lldb/source/ValueObject/ValueObject.cpp b/lldb/source/ValueObject/ValueObject.cpp
index 51eb5fb8b9dc2..1b0ef3d26f2bd 100644
--- a/lldb/source/ValueObject/ValueObject.cpp
+++ b/lldb/source/ValueObject/ValueObject.cpp
@@ -1224,11 +1224,17 @@ llvm::Expected<bool> ValueObject::GetValueAsBool() {
     auto value_or_err = GetValueAsAPSInt();
     if (value_or_err)
       return value_or_err->getBoolValue();
+    else
+      LLDB_LOG_ERROR(GetLog(LLDBLog::Types), value_or_err.takeError(),
+                     "GetValueAsAPSInt failed: {0}");
   }
   if (HasFloatingRepresentation(val_type)) {
     auto value_or_err = GetValueAsAPFloat();
     if (value_or_err)
       return value_or_err->isNonZero();
+    else
+      LLDB_LOG_ERROR(GetLog(LLDBLog::Types), value_or_err.takeError(),
+                     "GetValueAsAPFloat failed: {0}");
   }
   if (val_type.IsArrayType())
     return GetAddressOf().address != 0;
@@ -1311,14 +1317,14 @@ void ValueObject::SetValueFromInteger(lldb::ValueObjectSP new_val_sp,
     if (value_or_err)
       SetValueFromInteger(*value_or_err, error, can_update_var);
     else
-      error = Status::FromErrorString("error getting APSInt from new_val_sp");
+      error = Status::FromError(value_or_err.takeError());
   } else if (HasFloatingRepresentation(new_val_type)) {
     auto value_or_err = new_val_sp->GetValueAsAPFloat();
     if (value_or_err)
       SetValueFromInteger(value_or_err->bitcastToAPInt(), error,
                           can_update_var);
     else
-      error = Status::FromErrorString("error getting APFloat from new_val_sp");
+      error = Status::FromError(value_or_err.takeError());
   } else if (new_val_type.IsPointerType()) {
     bool success = true;
     uint64_t int_val = new_val_sp->GetValueAsUnsigned(0, &success);
diff --git a/lldb/source/ValueObject/ValueObjectMemory.cpp b/lldb/source/ValueObject/ValueObjectMemory.cpp
index 8a8a5e4e7aa9f..83cb4a27d0130 100644
--- a/lldb/source/ValueObject/ValueObjectMemory.cpp
+++ b/lldb/source/ValueObject/ValueObjectMemory.cpp
@@ -12,6 +12,7 @@
 #include "lldb/Target/ExecutionContext.h"
 #include "lldb/Target/Target.h"
 #include "lldb/Utility/DataExtractor.h"
+#include "lldb/Utility/LLDBLog.h"
 #include "lldb/Utility/Scalar.h"
 #include "lldb/Utility/Status.h"
 #include "lldb/ValueObject/ValueObject.h"
@@ -158,6 +159,9 @@ llvm::Expected<uint64_t> ValueObjectMemory::GetByteSize() {
     if (auto size =
             m_type_sp->GetByteSize(exe_ctx.GetBestExecutionContextScope()))
       return *size;
+    else
+      LLDB_LOG_ERROR(GetLog(LLDBLog::Types), size.takeError(),
+                     "failed to get byte size from type: {0}");
     return llvm::createStringError("could not get byte size of memory object");
   }
   return m_compiler_type.GetByteSize(exe_ctx.GetBestExecutionContextScope());