Millions of Americans bore the brunt of these failed talks as the weekly federal $600 unemployment boost expired in July and an eviction moratorium for federally subsidized housing also ended.
The orders -- one executive order and the other three memoranda -- address four categories: jobless aid, evictions, student loans and Social Security payroll taxes.
Here is a breakdown of each:
This memorandum reinstates the federal jobless aid bonus but will reduce weekly payments from $600 to $400.
Trump said states will be asked to cover 25% of the cost and can use federal funds allocated through the CARES Act, the $2.2 trillion economic stimulus bill signed into law in March.
It is unclear how that will be enforced, but Trump said it would be up to states to determine how much, if any of it to fund.
It is also unclear when Americans will see these renewed benefits in their bank accounts but Trump said action will be "very rapid."
The expired $600-per-week bonus unemployment benefit, a part of the CARES Act, when the COVID-19 pandemic began, helped prop up the economy while staving off financial disaster for millions of people thrown out of work.
House Democrats wanted to extend the boost in the new stimulus package, while Senate Republicans wanted to reduce it to $200.
This memorandum reduces the 7.65% Social Security and Medicare payroll tax to boost take-home paychecks until the end of the year.
The president said this will affect paychecks from Aug. 1 until the end of 2020.
Trump did not explain how he'd fund the Medicare and Social Security benefits that the 7% tax on employee income covers.
Trump faced bipartisan opposition when he pitched the payroll tax cut in March but continued to push hard as stimulus talks continued.
The memorandum allows borrowers with federally held student loans to have the option of deferring payments with no penalty.
This will be extended through the end of 2020 and "most likely" beyond the end of the year, Trump said.
The only executive order of the bundle will extend the freeze on evictions.
Millions of Americans are having difficulty making rent or mortgage payments. More than 12 million renters living in federally subsidized apartments or units with federally backed mortgages lost that safety net when the federal eviction moratorium expired on July 25.
Without moratoriums, landlords can initiate eviction proceedings in 30 days.
The Associated Press contributed to this report.